Naphthalene derivative and liquid crystal composition comprising the same

ABSTRACT

Disclosed in a novel liquid-crystalline compound which is a naphthalene derivative useful as an electro-optical liquid crystal display material, a liquid crystal composition containing such naphthalene derivatives and a liquid crystal display device comprising the same. The naphthalene derivative provided by the present invention exhibits an excellent liquid-crystallinity and miscibility with currently widely used liquid crystal compositions or compositions. The addition of the naphthalene derivative makes it possible to drastically lower the threshold voltage of the liquid crystal composition while maintaining its high response. The naphthalene derivative of the present invention is characterized by a large birefringence index. Further, most of the naphthalene derivative of the present invention has no strongly polar group in its molecule and thus can also be used for active matrix driving. Moreover, as shown in the foregoing examples, the naphthalene derivative of the present invention can be easily produced and is colorless and chemically stable. Accordingly, the liquid crystal composition comprising the naphthalene derivative of the present invention is extremely useful as a practical liquid crystal composition, particularly a liquid crystal composition which can operate within a wide temperature range and requires a high speed response and a low voltage driving.

This application is a division of prior application Ser. No. 09/296,550filed Apr. 22, 1999 now U.S. Pat. No. 6,468,607.

FIELD OF THE INVENTION

The present invention relates to a novel liquid-crystalline compoundwhich is a naphthalene derivative useful as an electro-optical liquidcrystal display material, a liquid crystal composition containing suchnaphthalene derivatives and a liquid crystal display device comprisingthe same.

BACKGROUNDS OF THE INVENTION

A liquid crystal display device has been used more and more in watch andelectronic calculator as well as various measuring instrument, panel forautomobile, word processor, electronic note, printer, computer,television, etc. Representative examples of liquid crystal displaysystem include TN (twisted nematic) system, STN (super-twisted nematic)system, DS (dynamic scattering) system, GH (guest-host) system, and FLC(ferroelectric liquid crystal) system, which allows high speed response.Referring to driving system, multiplex driving has been more common thanthe conventional static driving. Further, simple matrix system has beenrecently put into practical use. Moreover, active matrix system has beenput into practical use.

As the liquid crystal materials to be incorporated in these liquidcrystal display devices there have been synthesized a very large numberof kinds of liquid-crystalline compounds to date. Theseliquid-crystalline compounds are used depending on their display systemsdriving systems or purposes. However, the requirement for improvement ofthe properties of liquid crystal display device (enhancement of displayquality or increase of the size of display) has been growing more andmore. In order to satisfy these requirements, the development of nowliquid crystal compounds are under way.

A liquid crystal compound is composed of a central skeleton moietygenerally called core and a terminal moiety at both ends thereof. Ingeneral, the majority of the ring structure constituting the core moietyof a liquid crystal compound is occupied by 1,4-phenylene group (whichmay be substituted by one or two halogen atoms, cyano groups, methylgroups, etc.) and trans-1,4-cyclohexylene group. However, aliquid-crystalline compound merely made of 1,4-phenylene group andtrans-1,4-cyclohexylene group is limited in its kind or properties. As amatter of fact these components cannot sufficiently meet the foregoingdemands.

Besides the ring structures such as 1,4-phenylene group andtrans-1,4-cyclohexylene group, heterocyclic groups such aspyridine-2,5-diyl group, pyrimidine-2,5-diyl group and1,3-dioxane-trans-2,5-diyl group, condensed rings such astrans-decahydronaphthalene-2,6-diyl group, naphthalene-2,6-diyl group,tetrahydronaphthalene-2,6-diyl group, bicyclo[2,2,2]octane-1,4-diylgroup and spiro[3,3]heptane-2,6-diyl group, etc. have been under study.However, few of these compounds have been put into practical use due toproblems in production (technique, cost, etc.) and stability.

Though being a ring structure which has long bean reported,naphthalene-2,6-diyl group among these condensed rings is little knownfor properties other than liquid crystallinity (phase transitiontemperature), particularly nematic liquid crystallinity. (For smecticliquid crystal, it has recently been reported that an optically activealcohol ester of naphthalenecarboxylic acid exhibits interestingproperties as a ferroelectric liquid crystal.)

An ordinary liquid crystal compound is terminated by a chain (sidechain) group at one and thereof at least. A so-called p-type liquidcrystal the dielectric anisotropy of which is positive is mostlyterminated by a polar group at the other end thereof.

In order to lower the driving voltage in TN or STY display system aso-called strong P-type compound (the dielectric anisotropy of which ispositive and great) is required. For this purpose, a compound terminatedby cyano group at the molecular end thereof and having one or morefluorine atoms in the same direction per molecule is normally used. As anaphthalene derivative there has been reported only a compound havingphenylnaphthalene skeleton (GB2271771A: Citation (a)). There is noreference to physical properties and application.

As the foregoing P-type compound to be used in active matrix drivingthere is used a compound containing as a polar group fluorine atom,fluoroalkoxyl group or fluoroalkyl group alone. As a naphthalenederivative there is described only a compound having phenylnaphthaleneskeleton in GB2227019B (Citation (b)) and the above Citation (a).However, there is little reference to specific physical properties.Further, there is no reference to application to active matrix system.

In general, a liquid-crystalline compound which is a naphthalenederivative mostly exhibits a poor miscibility with other liquid crystalcompounds. It is thought effective to introduce side substituents(preferably fluorine atom in particular) into the naphthalene skeletonfor the purpose of improving the miscibility of the naphthalenederivative. The substitution by fluorine atom is thought effective alsoif an end polar group is directly introduced into the naphthalene ringin the application to the foregoing active matrix system. Some examplesof such a fluoronaphthalene derivative are shown in the foregoingCitation (a). However, there is little reference to production process,not to mention physical properties. Thus, it is by no means thought thatthese exemplified compounds are actually produced compounds. Further, itcannot be presumed what properties these compounds have. No compoundshaving a structure having a fluoroalkoxyl group or fluoroalkyl groupdirectly connected to naphthalene ring as a polar group have been known.

It has been known that a liquid crystal compound having an alkenyl groupinstead of an alkyl group, which is normally used as a side chainmoiety, exhibits excellent improvements such as improved liquidcrystallinity, reduced viscosity and improved sharpness in display.However, these alkenyl groups are mostly introduced directly connectedto cyclohexane ring. Thus, no compounds having alkenyl groups introducedin naphthalene ring have been reported.

Similarly, no naphthalene derivatives having as side chain alkoxylalkylgroup, fluoroalkyl group, fluoroalkenyl group, fluoroalkenyloxy group,etc. have been reported.

As groups connecting the ring structures in the core moiety of a liquidcrystal compound, there have been known many divalent organic groupsbesides single bond and 1,2-ethylene group (—CH₂CH₂—).

Liquid crystal compounds having 1,4-butylene group or 1,2-propylenegroup are known to have a low melting point and an excellent miscibilitywith other liquid crystal compounds as compared with the correspondingliquid crystal compounds having single bond or ethylene group. However,no liquid-crystalline compounds having 1,4-butylene group or1,2-propylene group have been known among naphthalene derivatives.

It has been reported that a liquid crystal compound havingdifluoroxymethylene group (—CF₂O—, —OCF₂—) or difluoroethenyl group(—CF═CF—) exhibits a low viscosity and thus is effective for theenhancement of response. However, no such naphthalene derivatives havebeen known.

SUMMARY OF THE INVENTION

An object of the present invention is to provide a novelliquid-crystalline compound having a naphthalene ring and a practicalliquid crystal composition comprising the same.

The present invention has the following constitutions to accomplish theforegoing object:

1. A naphthalene derivative represented by the following general formula(I):

wherein R^(a) represents a C₁₋₂₀ alkyl, alkoxy, alkoxyalkyl, alkenyl oralkenyloxy group which maybe substituted by a C₁₋₇ alkoxyl group or from1 to 7 fluorine atoms; a and b each represent an integer of 0 or 1 andsatisfy the relationship a≧b; rings A and B each independently representa trans-1,4-cyclohexylene group, 1,4-phenylene group which may besubstituted by one or more fluorine atoms, pyridine-2,5-diyl group,pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, pyridazine-3,6-diylgroup, trans-1,3-dioxane-2,5-diyl group,trans-decahydronaphthalene-2,6-diyl group ortetrahydronaphthalene-2,6-diyl group; L^(a) and L^(b) each independentlyrepresent —CH₂CH₂—, —CH₂CH₂CH₂CH₂—, —CH═CH—, —CH═CHCH₂CH₂—,—CH₂CH₂CH═CH—, —CH(CH₃)CH₂—, —CH₂CH₂(CH₃)—, —CF═CF—, —CF₂O—, —OCF₂—,—COO—, —OCO—, —C≡C— or single bond; X¹ to X⁶ each independentlyrepresent a hydrogen atom or fluorine atom; and Z^(a) represents afluorine atom, chlorine atom, trifluoromethoxy group, C₁₋₇ alkoxylgroup, C₁₋₂₀ alkyl, alkoxyl, alkenyl or alkenyloxy group which may besubstituted by from 1 to 7 fluorine atoms or group represented by thefollowing general formula (IIa) or (IIb):

wherein L^(c) and L^(d) each independently represent —CH₂CH₂—,—CH₂CH₂CH₂CH₂—, —CH═CH—, —CH═CHCH₂CH₂—, —CH₂CH₂CH═CH—, —CH(CH₃)CH₂—,—CH₂CH(CH₃)—, —CF═CF—, —CF₂O—, —OCF₂—, —COO—, —OCO—, —C≡C— or singlebond; rings C and D each independently represent atrans-1,4-cyclohexylene group, 1,4-phenylene group which may besubstituted by one or more fluorine atoms, pyridine-2,5-diyl group,pyrimidine-2,5diyl group, pyrazine-2,5-diyl group, pyridazine-3,6-diylgroup, trans-1,3-dioxane-2,5-diyl group,trans-decahydronaphthalene-2,6-diyl group ortetrahydronaphthalene-2,6-diyl group; Z^(b) and Z^(c) each independentlyrepresent a fluorine atom, chlorine atom, bromine atom, iodine atom,hydrogen atom, cyano group, —SCN, —OCN, —R′, —OR′, —OCOR′ or —COOR′,wherein R′ represents a C₁₋₂₀ alkyl or alkoxy group or C₂₋₂₀ alkenyl oralkenyloxy group, and these groups may be substituted by a C₁₋₁₀alkoxyl, acyl, acyloxy or alkoxycarbonyl group and one or more hydrogenatoms contained in these groups may be substituted by one or morefluorine atoms, and in the case of forming an asymmetric carbon by thesubstitution or branching, it may form an optically active form orracemic form, with the proviso that (1) if Z^(a) represents a grouprepresented by the general formula (IIa), b is 0, if Z^(a) represents agroup represented by the general formula (IIb), a is 0, and if Z^(a)represents a fluorine atom, chlorine atom, trifluoromethoxy group, C₁₋₇alkoxyl group or C₁₋₂₀ alkyl, alkoxyl, alkenyl or alkenyloxy group whichmay be substituted by from 1 to 7 fluorine atoms, a is 1; (2) if Z^(a)represents the group represented by the general formula (IIa), ring Crepresents a 1,4-phenylene group which may be substituted by fluorineatom and Z^(b) represents a fluorine atom, chlorine atom,trifluoromethoxy group or an alkyl or alkoxyl group which may besubstituted by fluorine atom, L^(a) represents —CH₂CH₂CH₂CH₂—, —CH═CH—,—CH═CHCH₂CH₂—, —CH₂CH₂CH═CH—, —CH(CH₃)CH₂—, —CH₂CH(CH₃)—, —CF═CF—,—CF₂O— or —OCF₂— and/or at least one of X¹ to X⁶ represents a fluorineatom; (3) if Z^(a) represents an alkyl or alkoxyl group, at least one ofX¹ to X⁶ represents a fluorine atom and/or L^(c) represents—CH₂CH₂CH₂CH₂—, —CF═CF—, —CF₂O— or —OCF₂—; (4) if Z^(a) represents afluorine or chlorine atom, L^(a) represents a single bond; and if ring Arepresents a 1,4-phenylene group which may be substituted by fluorineatom, b represents 0, or b represents 1 and L^(b) represents a singlebond; and (5) if a and b each represent 0, X¹ represents a fluorine atomand X² to X⁵ each represent a hydrogen atom; and if L^(c) represents asingle bond, Z^(b) represents fluorine atom, chlorine atom, hydrogenatom, trifluoromethoxy group, alkenyl group, alkenyloxy group, cyanatogroup or cyano group.

2. The compound according to Clause 1 above, wherein in the generalformula (I) a and b each represent 1.

3. The compound according to Clause 1 above, wherein in the generalformula (I) a is 1, b is 0 and Z^(a) is a group selected from the groupconsisting of fluorine atom, chlorine atom, trifluoromethoxy group, andC₁₋₂₀ alkyl, alkoxyl, alkenyl or alkenyloxy group which may besubstituted by C₁₋₇ alkoxyl group or from 1 to 7 fluorine atoms.

4. The compound according to Clause 1 above, wherein in the generalformula (I) a is 1, b is 0 and Z^(a) is a group represented by thegeneral formula (IIa).

5. The compound according to Clause 1 above, wherein in the generalformula (I) a and b each are 0 and Z^(a) represents a group representedby the general formula (IIa).

6. The compound according to Clause 1 above, wherein in the generalformula (1) a and b each are 0 and Z^(a) represents a group representedby the general formula (IIb).

7. The compound according to any one of Clauses 1 to 6 above, whereinL^(a), L^(b), L^(c) and L^(d) in the general formula (I) eachindependently represent a group selected from the group consisting of—CH₂CH₂— and single bond.

8. The compound according to any one of Clauses 1 to 4 and 7 above,wherein ring A in the general formula (I) represents a group selectedfrom the group consisting of trans-1,4-cyclohexylene group,1,4-phenylene group, 2-fluoro-1,4-phenylene group,2,6-difluoro-1,4-phenylene group and trans-decahydronaphthalene-2,6-diylgroup.

9. The compound according to any one of Clauses 1, 2, 7 and 8 above,wherein ring B in the general formula (I) represents atrans-1,4-cyclohexylene group.

10. The compound according to any one of Clauses 1 and 4 to 7 above,wherein rings C and D in the general formula (I) each independentlyrepresent a group selected from the group consisting of 1,4-phenylenegroup, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group,2,3-difluoro-1,4-phenylene group and 3,5-difluoro-1,4-phenylene group.

11. The compound according to any one of Clauses 1 to 3 and 7 to 9above, wherein Z^(a) in the general formula (I) represents a groupselected from the group consisting of C₄₋₁₂ alkenyl group which may besubstituted by from 1 to 3 fluorine atoms and C₃₋₁₂ alkenyloxy groupwhich may be substituted by from 1 to 3 fluorine atoms.

12. The compound according to any one of Clauses 1 to 3 and 7 to 9above, wherein Z^(a) in the general formula (I) represents a groupselected from the group consisting of C₁₋₁₂ alkyl or alkoxyl group whichmay be substituted by from 1 to 7 fluorine atoms.

13. The compound according to Clause 12 above, wherein Z^(a) in thegeneral formula (I) represents a trifluoromethoxy group.

14. The compound according to any one of Clauses 1 to 13 above, whereinX¹ in the general formula (I) represents a fluorine atom.

15. The compound according to Clause 14 above, wherein X² in the generalformula (I) represents a fluorine atom.

16. The compound according to Clause 2 or 3 above, wherein X¹ and X² inthe general formula (I) each represent a fluorine atom.

17. A liquid crystal composition comprising a compound represented bythe general formula (I) described in Clause 1 above.

18. The liquid crystal composition described in Clause 17 above for usein active matrix driving.

19. A liquid crystal device comprising as a constituent element a liquidcrystal composition described in Clause 17 above.

20. An active matrix driving liquid crystal display device comprising aliquid crystal composition described in Clause 18 above.

In more detail, the present invention provides a novelliquid-crystalline compound which is a naphthalene derivativerepresented by the following general formula (I):

In the foregoing general formula (I), R^(a) represents a C₁₋₂₀ alkyl,alkoxy, alkoxyalkyl, alkenyl or alkenyloxy group which may besubstituted by a C₁₋₇ alkoxyl group or from 1 to 7 fluorine atoms. R^(a)preferably is a C₁₋₇straight-chain alkyl or alkenyl group. The alkylgroup is preferably an unsubstituted alkyl group or an alkyl groupterminated by a plurality of fluorine atoms, particularly anunsubstituted alkyl group. The alkenyl group, if the ring structure towhich it is directly connected is a saturated ring, is preferably a1-alkenyl group or 3-alkenyl group. In this case, the double bond ispreferably at the end of side chain. Alternatively, the configuration ofthe double bond is preferably in trans-position. A particularlypreferred example of the alkenyl group is a vinyl group or 3-butenylgroup. Further, the hydrogen atom which is directly connected to thedouble bond is preferably substituted by a fluorine atom. Preferredexamples of such a substituted alkenyl group include (E)-2-fluorovinylgroup, 2,3-difluorovinyl group, 3-fluoro-2-propenyl group,3,3-difluoro-2-propenyl group, 4-fluoro-3-butenyl group, and4,4-difluoro-3-butenyl group. The alkenyl group, if the ring structureto which it is directly connected is an aromatic ring, is preferably a3-alkenyl group. In this case, the double bond is preferably at the endof side chain. Alternatively, the configuration of the double bond ispreferably in trans-position. A particularly preferred example of thealkenyl group is a 3-butenyl group or trans-3-pentenyl group.

a and b each represent 0 or 1 and satisfy the relationship a≧b.

Rings A and B each independently represent a trans-1,4-cyclohexylenegroup, 1,4-phenylene group which may be substituted by one or morefluorine atoms, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group,pyrazine-2,5-diyl group, pyridazine-3,6-diyl group,trans-1,3-dioxane-2,5-diyl group, trans-decahydronaphthalene-2,6-diylgroup or tetrahydronaphthalene-2,6-diyl group. Preferred among thesegroups are trans-1,4-cyclohexylene group, 1,4-phenylene,2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group,2,3-difluoro-1,4-phenylene group, 2,6-difluoro-1,4-phenylene group, andtrans-decahydro naphthalene-2,6-diyl group. In particular, ring B ispreferably a cyclohexane ring. Ring A, if a strong p-type liquid crystalcomposition is particularly required, is preferably a2-fluoro-1,4-phenylene group or 2,6-difluoro-1,4-phenylene group. If astrong n-type (negative dielectric anisotropy) is particularly required,ring A is preferably a 3-fluoro-1,4-phenylene group or2,3-difluoro-1,4-phenylene group.

L^(a) and L^(b) each independently represent —CH₂CH₂—, —CH₂CH₂CH₂CH₂—,—CH═CH—, —CH═CHCH₂CH₂—, —CH₂CH₂CH═CH—, —CH(CH₃)CH₂—, —CH₂CH(CH₃)—,—CF═CF—, —CF₂O—, —OCF₂—, —COO—, —OCO—, —C≡C— or single bond. Preferredamong these groups are —CH₂CH₂—, —CF═CF—, —CF₂O—, —OCF₂— and singlebond, and —CH₂CH₂— and single bond are particularly preferred. If L^(a)and L^(b) are present at the same time, at least one of them is morepreferably a single bond.

X¹ to X⁶ each independently represent a hydrogen atom or fluorine atom.In particular, X¹ preferably represents a fluorine atom. If theliquid-crystalline compound is a p-type compound, one or more of X¹ toX³ each are preferably a fluorine atom while X⁴ to X⁶ each arepreferably a hydrogen atom. Further, if Z^(a) is a polar group such asfluorine atom, X¹ and X² or X¹ to X³ each preferably represent afluorine atom at the same time. If the liquid-crystalline compound is an-type compound, at least one of X⁴ to X⁶ is preferably a fluorine atom.Alternatively, all X¹ to X⁶ each represent a hydrogen atom.Alternatively, X¹ is preferably a fluorine atom while the others areeach preferably a hydrogen atom.

Z^(a) represents a fluorine atom, chlorine atom, trifluoromethoxy group,C₁₋₇ alkoxyl group, C₁₋₂₀ alkyl, alkoxyl, alkenyl or alkenyloxy groupwhich may be substituted by from 1 to 7 fluorine atoms or grouprepresented by the following general formula (IIa) or (IIb):

Preferred among these groups are fluorine atom, trifluoromethoxy group,difluoromethoxy group, C₁₋₇ straight-chain alkyl group, C₁₋₃straight-chain alkoxyl group, C₄₋₇ straight-chain 3-alkenyl group, C₃₋₇straight-chain alkenyloxy group, and group represented by the foregoinggeneral formula (IIa) or (IIb). Particularly preferred among thesegroups are fluorine atom, trifluoromethoxy group, methyl group, ethylgroup, propyl group, butyl group, pentyl group, methoxy group, ethoxygroup, 3-butenyl group, trans-3-pentenyl group, allyloxy group,crotyloxy group, and group represented by the general formula (IIa).

In the general formula (IIa) or (IIb), L^(c) and L^(d) eachindependently represent —CH₂CH₂—, —CH₂CH₂CH₂CH₂—, —CH═CH—,—CH═CHCH₂CH₂—, —CH₂CH₂CH═CH—, —CH(CH₃)CH₂—, —CH₂CH(CH₃)—, —CF═CF—,—CF₂O—, —OCF₂—, —COO—, —OCO—, —C≡C— or single bond. Preferred amongthese groups are —CH₂CH₂—, —CF═CF—, —CF₂O—, —OCF₂— or single bond.Particularly preferred among these groups are —CH₂CH₂— or single bond.Further, if L^(c) and L^(d) are present at the same time, or if L^(c)and the foregoing L^(a) are present at the same time, at least one ofthem is preferably a single bond.

Rings C and D each independently represent a trans-1,4-cyclohexylenegroup, 1,4-phenylene group which may be substituted by one or morefluorine atoms, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group,pyrazine-2,5-diyl group, pyridazine-3,6-diyl group,trans-1,3-dioxane-2,5-diyl group, trans-decahydronaphthalene-2,6-diylgroup or tetrahydronaphthalene-2,6-diyl group. Preferred among thesegroups are trans-1,4-cyclohexylene group and 1,4-phenylene group whichmay be substituted by one or more fluorine atoms. Particularly preferredamong these groups are 1,4-phenylene group, 2-fluoro-1,4-phenylenegroup, 3-fluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group,and 3,5-difluoro-1,4-phenylene group. In particular, if theliquid-crystalline compound is a p-type compound, rings C and D each arepreferably a 3-fluoro-1,4-phenylene group or 3,5-difluoro-1,4-phenylenegroup.

Z^(b) and Z^(c) each independently represent a fluorine atom, chlorineatom, bromine atom, iodine atom, hydrogen atom, cyano group, —SCN, —OCN,—R′, —OR′, —OCOR′ or —COOR′, wherein R′ represents a C₁₋₂₀ alkyl oralkoxy group or C₂₋₂₀ alkenyl or alkenyloxy group, and these groups maybe susbstituted by a C₁₋₁₀ alkoxyl, acyl, acyloxy or alkoxycarbonylgroup and one or more hydrogen atoms contained in these groups may besubstituted by one or more fluorine atoms, and in the case of forming anasymmetric carbon by the substitution or branching, it may form anoptically active form or racemic form.

Preferably, Z^(b) and Z^(c) each represent a fluorine atom, chlorineatom, hydrogen atom, trifluoromethoxy group, C₁₋₇ alkoxyl group or C₁₋₂₀alkyl, alkoxyl, alkenyl or alkenyloxy group which may be substituted byfrom 1 to 20 fluorine atoms, cyanato group or cyano group. Preferredamong these groups are fluorine atom, trifluoromethoxy group,difluoromethoxy group, C₁₋₇, straight-chain alkyl group, C₁₋₃straight-chain alkoxyl group, C₄₋₇ straight-chain 3-alkenyl group, C₃₋₇straight-chain alkenyloxy group or cyano group. Particularly preferredamong these groups are fluorine atom, trifluoromethoxy group, methylgroup, ethyl group, propyl group, butyl group, pentyl group, methoxygroup, ethoxy group, 3-butenyl group, trans-3-pentenyl group, allyloxygroup, crotyloxy group, and cyano group.

There are the following provisions:

(1) If Z^(a) represents the group represented by the general formula(IIa), b is 0, if Z^(a) represents the group represented by the generalformula (IIb), a is 0, and if Z^(a) represents a fluorine atom, chlorineatom, trifluoromethoxy group, C₁₋₇ alkoxyl group or C₁₋₂₀ alkyl,alkoxyl, alkenyl or alkenyloxy group which may be substituted by from 1to 7 fluorine atoms, a is 1;

(2) If Z^(a) represents the group represented by the general formula(IIa), ring C represents a 1,4-phenylene group which may be substitutedby fluorine atom and Z^(b) represents a fluorine atom, chlorine atom,trifluoromethoxy group or an alkyl or alkoxyl group which may besubstituted by fluorine atom, L^(c) represents —CH₂CH₂CH₂CH₂—, —CH═CH—,—CH═CHCH₂CH₂—, —CH₂CH₂CH═CH—, —CH(CH₃)CH₂—, —CH₂CH(CH₃)—, —CF═CF—,—CF₂O— or —OCF₂— and/or at least one of X¹ to X⁶ represents a fluorineatom;

(3) If Z^(a) represents an alkyl or alkoxyl group, at least one of X¹ toX⁶ represents a fluorine atom and/or L^(c) represents —CH₂CH₂CH₂CH₂—,—CF═CF—, —CF₂O— or —OCF₂—;

(4) if Z^(a) represents a fluorine or chlorine atom, L^(a) represents asingle bond; and if ring A represents a 1,4-phenylene group which may besubstituted by fluorine atom, b represents 0, or b represents 1 andL^(b) represents a single bond; and

(5) If a and b each represent 0, X¹ represents a fluorine atom and X² toX⁶ each represent a hydrogen atom; and if L^(c) represents a singlebond, Z^(b) represents fluorine atom, chlorine atom, hydrogen atom,trifluoromethoxy group, alkenyl group, alkenyloxy group, cyanato groupor cyano group.

As mentioned, there are a variety of compounds represented by thegeneral formula (I). Preferred are those represented by the followinggeneral formulae (Ia) to (Ie) as classified by the structure of coremoiety:

wherein R^(a), ring A, ring B, L^(a), L^(b), Z^(b), Z^(c) and X¹ to X⁶are as defined in the general formula (I); ring C and ring D are asdefined in the general formula (IIa) or (IIb); and Z^(d) represents afluorine atom, chlorine atom, trifluoromethoxy group, C₁₋₇ alkoxyl groupor C₁₋₂₀ alkyl, alkoxyl, alkenyl or alkenyloxy group which may besubstituted by from 1 to 7 fluorine atoms.

Particularly preferred among the compounds represented by the generalformula (Ia) are those shown below.

Particularly preferred among the compounds represented by the generalformula (Ib) are those shown below.

Particularly preferred among the compounds represented by the generalformula (Ic) are those shown below.

Particularly preferred among the compounds represented by the generalformula (Id) are those shown below.

Particularly preferred among the compounds represented by the generalformula (Ie) are those shown below.

In the foregoing general formulae, R is as defined above, and R′represents a C₁₋₇ straight-chain alkyl group or C₂₋₇ straight-chainalkenyl group, particularly vinyl group or 3-butenyl group.

Particularly preferred among the foregoing compounds are thoserepresented by the general formulae (Iaaa), (Iaad), (Iaae), (Iacb),(Iagb), (Iaib), (Iana), (Ianb), (Iand), (Iapa), (Iapb), (Iata), (Iatb),(Iatd), (Iava), (Iavb), (Iawa), (Iawb), (Iawd), (IaAa), (IaAb), (IaAd),(IaCa), (IaCb), (InGa), (IaGb), (IaGd), (IaJa), (IaJb), (IaJd), (IaNa),(IaNb), (IaNd), (IaPa), (IaPb), (IaPd), (IaTa), (IaTb), (IaTd), (IaVa),(IaVb), (IaVd), (IaZa) (IaZb), (IaZd), (Ibaa), (Ibab), (Ibad), (Ibca),(Ibcb), (Ibcd), (Ibea), (Ibeb), (Ibed), (Ibga), (Ibgb), (Ibgd), (Ibia),(Ibib), (Ibid), (Ibka), (Ibkb), (Ibkd), (Ibpa), (Ibpb), (Ibpd), (Ibsa),(Ibsb), (Ibsd), (Ibta), (Ibtb), (Ibtd), (Ibva), (Ibvb), (Ibvd), (Ibxa),(Ibxb), (Ibxd), (Icaa) to (Icim), and (Idaa) to (Idcm).

The compound represented by the general formula (I) of the presentinvention can be prepared by the following synthesis processes incombination depending on R, rings A and B, L^(a) and L^(b).

[I] Process for the Synthesis of Compounds Represented by the GeneralFormulae (Iaaa) to (Iafe)

(1) Compound prepared from a group represented by the following generalformula (IIIa):

wherein R^(b) represents an alkyl group as a key intermediate

-   (i) A naphthalene derivative represented by the following general    formula (IVa):

wherein W^(a) represents a halogen atom such as chlorine, bromine andiodine, preferably bromine atom; and Y^(a) represents a phenolichydroxyl group protected by methoxy or benzyloxy group, hydrogen atom ortrifluoromethoxy group,is reacted with magnesium to produce a Grignard reagent or lithioatedwith an alkyl lithium such as butyl lithium to produce an organic metalreagent. The Grignard reagent or organic metal reagent thus prepared isthen reacted with a 4-alkylcyclohexanene represented by the followinggeneral formula (Va):

wherein R^(b) represents an alkyl group. Subsequently, the resultingcyclohexanol derivative is dehydrated in the presence of an acidcatalyst to obtain a cyclohexenylnaphthalene derivative represented bythe following general formula (IVa):

wherein R^(b) represents an alkyl group; and Y^(a) is as defined in thegeneral formula (IVa). The cyclohexenylnaphthalene derivative thusobtained is subjected to catalytic reduction, optionally subjected toisomerization of cyclohexane ring, and then freed of Y^(a), if it is aprotective group for phenolic hydroxyl group such as methoxy group, withhydrobromic acid to obtain a naphthol derivative represented by theforegoing general formula (IIIa).

-   (ii) The naphthol derivative (IIIa) obtained in the process (i) can    be reacted with a halogenated alkyl or halogenated alkenyl in the    presence of a base to obtain a compound represented by the general    formula (Iafa) wherein R is an alkyl group.-   (iii) The naphthol derivative (IIIa) obtained in the process (i) can    be reacted with trifluoromethanesulfonic anhydride or    trifluoromethanesulfonic acid chloride in the presence of a base    such as pyridine to obtain a sulfonate represented by the following    general formula (VIIa):

wherein R^(b) is as defined above; and Tf represents atrifluoromethanesulfonyl group.

-   (iv) The sulfonate (VIIa) can be reacted with an organic metal    reagent represented by the following general formula (VIIIa):    R^(b)-M^(a)  (VIIIa)    wherein R^(b) is as defined above; and M^(a) represents MgBr, MgCl,    MgI or Li, preferably MgBr, in the presence of a nickel catalyst to    obtain a compound represented by the general formula (Iaea) wherein    R is an alkyl group. Preferred examples of the nickel catalyst    employable herein include-   dichlorobis(triphenylphosphine)nickel (II),    dichloro[1,2-bis(triphenylphosphino)ethane]nickel (II), and tetrakis    (triphenylphosphine) nickel (0).-   (v) The naphthol derivative represented by the general formula    (IIIa) can be reacted with carbon disulfide in the presence of a    strong base, and then reacted with an alkylating agent to obtain a    dithiocarbonic acid ester represented by the following general    formula (IXa):

wherein R^(b) is as defined above; and R″ represents a lower alkylgroup. Preferred examples of the strong base employable herein includehydrogenated alkaline metal such as sodium hydride, alkyl lithium suchas butyl lithium, lithium amide such as lithium diisopropyl amide, andalcoholate such as potassium t-butoxide. Preferred examples of thealkylating agent employable herein include methyl iodide, ethyl iodide,methyl bromide, ethyl bromide, dimethyl sulfate, and methylp-toluenesulfonate. The dithiocarbonic acid ester thus obtained can thenbe reacted with fluoride ion in the presence of a halonium ion generatorto produce a compound represented by the foregoing general formula(Iaca) wherein R is an alkyl group. As the halonium ion generator theremay be used N-iodosuccinic acid imide (NIS), N-bromosuccinic acid imide(NBS), N-chlorosuccinic acid imide (NCS),1,3-dibromo-5,5-dimethylhydantoin (DBH) or the like. As the fluoride ionsource there may be used tetrabutylammonium dihydrotrifluoride(TBAH₂F₃), hydrogen fluoride-pyridine complex (HF-Py), hydrogenfluoride-melamine complex (HF-mel) or the like. If the dithiocarbonicacid ester has an aromatic ring, the aromatic ring may be halogenatedwith halonium ion. In this case, the halide thus obtained can belithioated with alkyl lithium such as butyl lithium, and then protonatedto obtain the desired compound.

-   (vi) The compound represented by the general formula (IIIa) obtained    in the foregoing process (i) can be reacted with ammonium in the    presence of sodium hydrogensulfide to obtain a compound represented    by the following general formula (Xa):

wherein R^(b) is as defined above. The compound (Xa) can then be reactedwith a fluorine source such as hydrofluoric acid in the form of nitriterepresented by the following general formula (XIa):

wherein R^(b) is as defined above, to obtain a compound represented bythe general formula (Iaaa).

-   (vii) The compound represented by the general formula (XIa) obtained    in the foregoing process (vi) can then be reacted with a chlorine    source such as copper chloride (I) to obtain a compound represented    by the foregoing general formula (Iaba) wherein R is an alkyl group.-   (viii) The naphthol derivative represented by the general formula    (IIIa) can be reacted with fluoride ion in the presence of a    halonium ion generator in the form of thioformic acid ester    represented by the following general formula (XIIa):

wherein R^(b) is as defined above to produce a compound represented bythe foregoing general formula (Iada) wherein R is an alkyl group. As thehalonium ion generator there may be used N-iodosuccinic acid imide(NIS), N-bromosuccinic acid imide (NBS), N-chlorosuccinic acid imide(NCS), 1,3-dibromo-5,5-dimethylhydantoin (DBH) or the like. As thefluoride ion source there may be used tetrabutylamoniumdihydrotrifluoride (TBAH₂F₃) hydrogen fluoride-pyridine complex (HP-Py),hydrogen fluoride-melamine complex (HF-mel) or the like. If thethioformic acid ester has an aromatic ring, the aromatic ring may behalogenated with halonium ion. In this case, the halide thus obtainedcan be lithioated with alkyl lithium such as butyl lithium, and thenprotonated to obtain the desired compound.

-   (ix) The naphthol derivative represented by the general formula    (IIIa) can be fluorinated with one equivalent of a fluorinating    agent such as N,N′-difluoro-2,2′-dipyridinium bistetrafluoroborate    and N-fluoro-5-trifluoromethoxy pyridinium-2-sulfonate to obtain a    compound represented by the following general formula (XIII):

and by-products represented by the following general formulas (XIVa) and(XVa):

wherein R^(b) is as defined above.

-   (x) The naphthol derivative represented by the general formula    (IIIa) can be fluorinated with two equivalents of a fluorinating    agent such as    1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane    bistetrafluoroborate and    1-fluoro-4-hydroxy-14-diazoniabicyclo[2,2,2]octane    bistetrafluoroborate to selectively obtain a compound represented by    the following general formula (XIVa):

wherein R^(b) is as defined above. The compound (XIVa) can then befluorinated with a fluorinating agent such as DAST and HF-pyridine toobtain a compound represented by the following general formula (XVIa):

wherein R^(b) is as defined above. The compound (XVIa) can then besubjected to catalytic reduction to obtain a compound represented by thegeneral formula (Iaad) wherein R is an alkyl group.

-   (xi) The compound (Iaad) obtained in the foregoing process (x) can    be lithioated with butyl lithium, and then reacted with a    fluorinating agent such as    1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2 2,2]octane    bistetrafluoroborate and    1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane    bistetrafluoroborate to obtain a compound represented by the general    formula (Iaae) wherein R is an alkyl group.-   (xii) The compound (XIIIa) shown in the foregoing process (ix) can    be converted to a sulfonate in accordance with the foregoing process    (iii), and then subjected to catalytic reduction to obtain a    compound represented by the general formula (Iaab) wherein R is an    alkyl group.-   (xiii) The compound (XVa) shown in the foregoing process (ix) can be    converted to a sulfonate in accordance with the foregoing process    (iii), and then subjected to catalytic reduction to obtain a    compound represented by the general formula (Iaag) wherein R is an    alkyl group.-   (xiv) The procedure of the foregoing process (vi) can be followed    except that the compound represented by the general formula (IVa) is    replaced by a compound represented by the following general formula    (XVIIa):

wherein W^(a) and Y^(a) are as defined above to obtain a compoundrepresented by the following general formula (XIXa):

wherein R^(b) is as defined above, via a compound represented by thefollowing general formula (XVIIIa):

wherein R^(b) is as defined above.The compound represented by the general formula (XIXa) can be nitratedwith a mixture of nitric acid and sulfuric acid, and then subjected toreduction to obtain a compound represented by the following generalformula (XXa):

wherein R^(b) is as defined above.

-   (xv) The compound (XXa) obtained in the foregoing process (xiv) can    be reacted with a nitrite to produce a compound represented by the    following general formula (XXIa):

wherein R^(b) is as defined above, and then reacted with a fluorinesource such as hydrofluoric acid to obtain a compound represented by thegeneral formula (Iaac).

-   (xvi) The compound (XXIa) obtained in the foregoing process (xv) can    be reacted with a chlorine source such as copper chloride (I) to    obtain a compound represented by the general formula (Iabc) wherein    R is an alkyl group.-   (xvii) The compound (XXIa) obtained in the foregoing process (xv)    can be reacted with water to obtain a compound represented by the    following general formula (XXIIa):

wherein R^(b) is as defined above.

-   (xviii) The compounds represented by the general formulae (XIIIa),    (XVa) and (XXa) can be processed in accordance with the foregoing    processes (ii) to (v), (vii) and (viii) to obtain compounds    represented by the general formulae (Iabb), (Iabd), (Iacb), (Iacc),    (Iacd), (Iadb), (Iadc), (Iadd), (Iaeb), (Iaec), (Iaed), (Iafb),    (Iafc) and (Iafd) wherein R is an alkyl group.-   (xix) The procedure of the processes (i) to (viii) can be followed    except that the compound (IVa) is replaced by the compound (XXIIIa):

wherein W^(a), Y^(a), X¹, X² and X³ are as defined above, to obtaincompounds represented by the general formulae (Iaaa) to (Iafe) wherein Ris an alkyl group.(2) Compound prepared from a group represented by the following generalformula (IIIb):

wherein R^(c) represents an alkenyl group as a key intermediate

-   (i) The naphthalene derivative represented by the general formula    (IVa) is reacted with magnesium to produce a Grignard reagent or    lithioated with an alkyl lithium such as butyl lithium to produce an    organic metal reagent. The Grignard reagent or organic metal reagent    thus prepared is then reacted with a compound represented by the    following general formula (Vb):

dehydrated in the presence of an acid catalyst, optionallyre-acetalated, subjected to catalytic reduction, and then deacetalatedto obtain a naphthylcyclohexyl cyclohexanene derivative represented bythe following general formula (XXIVb):

wherein Y^(a) is as defined above. The naphthylcyclohexyl cyclohexanenederivative (XXIVb) is reacted with a Wittig reagent represented by thefollowing general formula (XXVb):

and then hydrolyzed with an acid to obtain a cyclohexane carbaldehydederivative represented by the following general formula (XXVIb):

The cyclohexane carbaldehyde derivative represented by the generalformula (XXVIb) can be reacted with a Wittig reagent represented by thefollowing general formula (XXVIIb):CH₂═PPh₃  (XXVIIb),and then freed of phenolic hydroxyl group of Z^(a) to produce a compoundrepresented by the general formula (IIIb) wherein R^(b) is a vinylgroup. The cyclohexane carbaldehyde derivative (XXVIb) can be furtherreacted with the Wittig reagent (XXVb) twice, reacted with the Wittigreagent (XXVIIb), and then freed of phenolic hydroxyl group of Z^(a) toproduce a compound represented by the general formula (IIIb) whereinR^(b) is a 3-butenyl group.

-   (ii) The compound (IIIb) obtained in the process (2)-(i) can be    processed in accordance with the processes (1)-(i) to (1)-(viii) to    produce compounds represented by the general formulae (Iaaa) to    (Iafe) wherein R is an alkenyl group.    [II] Process for the Preparation of Compounds Represented by the    General Formulae (Iaga) to (Iane)    (1) Compound prepared from a group represented by the following    general formula (IIIc):

wherein R is as defined above as a key intermediate

-   (i) The naphthalene derivative represented by the following general    formula (IVa) is reacted with magnesium to produce a Grignard    reagent or lithioated with an alkyl lithium such as butyl lithium to    produce an organic metal reagent which is reacted with trimethyl    boron and then demethylated to obtain a boric acid derivative. The    Grignard reagent or boric acid derivative thus produced can be    reacted with a benzene derivative represented by the following    general formula (Vc):

wherein R is as defined above; and Y^(b) represents a releasing groupsuch as trifluoromethanesulfonyloxy of halogen atom such as chlorine,bromine and iodine, preferably trifluoromethanesulfonyloxy of bromine,in the presence of a transition metal catalyst, and then subjected todemethoxylation of Z^(a) to produce the desired compound.

Alternatively, the benzene derivative represented by the general formula(Vc) can be reacted with magnesium to produce a Grignard reagent orlithionatad with an alkyl lithium such as butyl lithium to obtain anorganic metal reagent, reacted with trimethyl boron, demethylated toobtain a boric acid derivative, and then reacted with a benzenederivative represented by the following general formula (IVb):

wherein W^(b) is as defined above in the presence of a transition metalcatalyst to produce the desired compound.

-   (ii) The procedure of the process [II]-(1)-(i) can be followed    except that the compound (IIIc) is replaced by the compound (XVIIa)    and the compound (IVb) is replaced by a compound represented by the    following general formula (IVb′):

wherein Z^(b) is as defined above, to obtain a compound represented bythe following general formula (XXVIIIb):

wherein R is as defined above.

-   (iii) The procedure of the above processes [I]-(1)-(ii) to    [I]-(1)-(xix) can be followed except that the compound (IIIa) is    replaced by the compound (IIIb) and the compound (XVIIIa) is    replaced by the compound (XVIIIb) to obtain compounds represented by    the general formulae (Iaga) to (Iane).    [III] Process for the Preparation of Compounds Represented by the    General Formulae (IaGa) to (IaMe), (IaZa) to (IaZe), (Ibaa) to    (Ibde) and (Ibva) to (Ibye)

The procedure of the above process [I] can be followed except that thecompound (Va) in replaced by compounds represented by the followinggeneral formulae (Vd) to (Vg):

wherein R^(b) is as defined above, and the compound (Vb) is replaced bycompounds represented by the following general formulae (Vd′) to (Vg′):

to obtain compounds represented by the general formulae (IaGa) to(IaMe), (IaZa) to (IaZe), (Ibaa) to (Ibde) and (Ibva) to (Ibye).[IV] Process for the Preparation of Compounds Represented by the GeneralFormulae (IaAa) to (IaFe), (IaNa) to (IaSe), (IaTa) to (IaXe) and (Ibsa)to (Ibue)

The procedure of the above process [I] can be followed except that thecompound (Va) is replaced by compounds represented by the followinggeneral formulae (Vh) to (Vk):

wherein R^(b) is as defined above, and the compound (Vb) is replaced bythe foregoing General Formulae (Vd′) to (Vg′) to obtain compoundsrepresented by the General Formulae (IaAa) to (IaFe), (IaNa) to (IaSe),(IaTa) to (IaXe) and (Ibsa) to (Ibue).[V] Process for the Preparation of Compounds Represented by the GeneralFormulae (Iana) to (Iase), (Iata) to (Iaye), (Ibea) to (Ibhe), (Ibfa) to(Ibme) and (Ibna) to (Ibqe)

The procedure of the above process [II] can be followed except that thecompound (Vc) is replaced by compounds represented by the followinggeneral formulae (Vm) to (Vr):

wherein R and Y^(b) are as defined above, to obtain compoundsrepresented by the General Formulae (Iana) to (Iases), (Iata) to (Iaye),(Ibea) to (Ibhe), (Ibfa) to (Ibme) and (Ibna) to (Ibqe).[VI] Process for the Preparation of Compounds Represented by the GeneralFormulae (Icaa) to (Icch)

-   (i) The procedure of the above process [I]-(i) can be followed    except that the compound (Va) is replaced by the compound    represented by the general formula (Vf) to obtain a compound    represented by the following general formula (XXIVa):

The procedure of the process [I]-(1)-(ix) can be followed except thatthe compound (IIIa) is replaced by the compound (XXIVa) to obtaincompounds represented by the following general formulae (XXva) and(XXVIa):

The compounds (XXIVa), (XXVa) and (XXVIa) can be reacted withtrifluoromethanesulfonic acid anhydride or trifluoromethane sulfonicacid chloride in the presence of a base such as pyridine to obtain asulfonate which is then allowed to undergo cross coupling reaction witha compound represented by the following general formula (XXVIIa):

wherein R^(f) represents a hydrogen atom, fluoro group, trifluoromethoxygroup, difluoromethoxy group or methoxy group; and E represents ahydrogen atom or fluorine atom, in the presence of a transition metalcatalyst to produce compounds represented by the general formulae (Icaa)to (Icaf), (Icba) to (Icbf), (Icca) to (Iccf), (XXVIIIa) and (XXIXa):

wherein E is as defined above.

The compound (XXVIIa) thus obtained can be deprotected with hydrobromicacid, and then reacted with trifluoromethanesulfonic acid anhydride ortrifluoromethane sulfonic acid chloride in the presence of a base suchas pyridine to obtain a sulfonate which is then reacted with coppercyanide (I) or reacted with sodium cyanide or potassium cyanide in thepresence of a transition metal catalyst to obtain compounds representedby the general formulae (Icag), (Icah), (Icbg), (Icbh), (Iccg) and(Icch).

[VII] Process for the Preparation of Compounds Represented by theGeneral Formulae (Icda) to (Iceh)

The procedure of the above process [VI] can be followed except that thecompound (Vf) is replaced by the compound (Vk) to produce compoundsrepresented by the general formulae (Icda) to (Iceh).

[VIII] Process for the Preparation of Compounds Represented by theGeneral Formulae (Icfa) to (Icgh)

-   (i) The procedure of the above process [II]-(1)-(i) can be followed    except that the compound (Vc) is replaced by the compound (Vp) to    obtain a compound represented by the following general formula    (XXXa):

-   (ii) The procedure of the above process [VI] can be followed except    that the compound (XXIVa) is replaced by the compound (XXXa) to    obtain compounds represented by the general formulae (Icfa) to    (Icgh).    [IX] Process for the Preparation of Compounds Represented by the    general formulae (Icha) to (Ichm), (Icia) to (Icim), (Idba) to    (Idbm) and (Idca) to (Idcm)

The procedure of the above process [VIII] can be followed except thatthe compound (Vp) is replaced by compounds represented by the GeneralFormulae (Vq), (Vr) and (Vs):R—Y^(b)  (Vs)to produce compounds represented by the general formulae (Icha) to(Ichm), (Icia) to (Icim), (Idba) to (Idbm) and (Idca) to (Idcm).[X]Process for the Preparation of Compounds Represented by the GeneralFormulae (Idba) to (Iefm)

The procedure of the above process [IX] can be followed except that thecompound (XXVIIa) is replaced by a compound represented by the followinggeneral formula (XXVIIb):

to produce compounds represented by the general formulae (Icfa) to(Icgh).

Specific representative examples of the compound (I) of the presentinvention thus produced will be set forth in Tables 1 to 3 belowtogether with their phase transition temperature.

TABLE 1 Compound represented by the general formula (Ib):

No.

PhaseTransitionTemperature (° C.) Ib-1

Cr 48 (N 39) I Ib-2

Cr 42 I Ib-3

C 69 N 142 I Ib-4

C 118 N 176 I

TABLE 2 Compound represented by the general formula (Ic): (Ic)

No.

PhaseTransitionTemperature (° C.) Ic-1

Cr 99 N 200.5 I Ic-2

Cr 85 N 198.5 I Ic-3

C 79 I Ic-4

Cr 92.5 N 158 I Ic-5

Cr 72.5 N 155.5 I Ic-6

Cr 110 N 166 I Ic-7

Cr 134.5 N 134 I

TABLE 3 Compound represented by the general formula (Id): (Id)

No.

PhaseTransitionTemperature (° C.) Id-1

Cr 62 I Id-2

Cr 50 I Id-3

C 112 (N 78.5) I Id-4

Cr 128 I Id-5

Cr 109 I Id-6

Cr 74 (N 63) I Id-7

Cr −16 N 13 I Id-8

Cr 69.5 I Id-9

Cr 38 I Id-10

Cr 27.5 I Id-11

Cr 70 S_(B) 113 S_(A) 119 I Id-12

Cr 113 I (Cr represents crystalline phase, N represents nematic phase,and I represents isotropic liquid phase.)

The effects exerted by the incorporation of the compound (I) in theliquid crystal composition will be described hereinafter.

The compound represented by the general formula (Ib-1) set forth inTable 1:

is added to a low viscosity host liquid crystal (H) having a wideoperating temperature range, particularly a host liquid crystal (H)suitable for active matrix driving represented by the following generalformula:

in an amount of 20% to prepare a nematic liquid crystal composition(M-1). The upper nematic phase temperature limit (T_(N-1)) was 98.2° C.The nematic liquid crystal composition (M-1) was allowed to stand at atemperature of 150° C. for 20 hours, and then measured for T_(N-1). Theresults were 97.8° C., demonstrating that the nematic liquid crystalcomposition (M-1) showed little or no change of T_(N-1) from beforeheating. The nematic liquid crystal composition (M-1) was irradiatedwith ultraviolet rays for 20 hours. However, the nematic liquid crystalcomposition (M-1) showed no change of T_(N-1). The composition was thenmeasured for voltage holding ratio. As a result, the compositionexhibited a sufficiently high voltage holding ratio similarly to thehost liquid crystal (H) during preparation, after heating and afterirradiation with ultraviolet rays.

Subsequently, the nematic liquid crystal composition (M-1) was filled ina TN cell having a thickness of 4.5 μm to prepare a liquid crystaldevice. The liquid crystal device was then measured for electro-opticalproperties. The results are as follows:

Upper nematic phase Temperature limit (T_(N-1)) 98.6° C. Dielectricanisotropy (Δε) 4.60 Threshold voltage (Vth) 1.76 V Response (τ) 21.5 msec.

On the other hand, the physical properties and electro-opticalproperties of the host liquid crystal (H) alone are as follows:

Upper nematic phase temperature limit (T_(N-1)) 116.7° C. Dielectricanisotropy (Δε) 4.80 Threshold voltage (Vth) 1.88 V Response (τ) 21.5 msec.

The term “response” as used herein is meant to indicate the responsetime shown during the application of voltage at which the rise time (τr)and the drop time (τd) are equal to each other. The results show thatthe compound (Ib-1) exhibits a smaller dielectric anisotropy than thehost liquid crystal (H) and a threshold voltage drop of about 10% fromthe host liquid crystal (H).

The compound represented by the general formula (Ib-2) set forth inTable 1:

was then added to the host liquid crystal (H) in the same amount asmentioned above (20%) to prepare a liquid crystal composition (M-2).

T_(N-1) of the nematic liquid crystal composition (M-2) and theelectro-optical properties of the liquid crystal device prepared in thesame manner as above from the composition (M-2) are as follows:

Upper nematic phase temperature limit (T_(N-1)) 92.7° C. Dielectricanisotropy (Δε) 5.7 Threshold voltage (Vth) 1.53 V Response (τ) 28.0 msec.

It can thus be seen that the compound (Ib-2) exhibits a smallerdielectric anisotropy than the host liquid crystal (H) and a thresholdvoltage drop of about 20% from the host liquid crystal (H).

The nematic liquid crystal composition (M-2) was then subjected tothermal stability test and ultraviolet ray irradiation test in the samemanner as the composition (M-1). As a result, the composition (M-2)showed no change of T_(N-1) after these tests. The nematic liquidcrystal composition (M-2) was then measured for voltage holding ratio.As a result, the composition (M-2) exhibited a sufficiently high voltageholding ratio during preparation, after heating and after irradiationwith ultraviolet rays.

As mentioned above, the compound represented by the general formula (I)is very useful in the preparation of a liquid crystal composition having(a) a wide nematic phase operating temperature range, (b) a thresholdvoltage low enough to drive at a low voltage, (c) a quick response and(d) a voltage holding ratio high enough for active matrix driving.

The compound represented by the general formula (Ic-7) set forth inTable 2:

was added to a host liquid crystal composition (H) having a wideoperating temperature range and a low viscosity which can be used alsoin active matrix driving in an amount of 20% by weight to prepare aliquid crystal composition (M-3). The physical properties of the hostliquid crystal composition (H) and the electro-optical properties of theliquid crystal device prepared therefrom are as follows:

T_(N-1): 116.7° C. T_(C-N): +11° C. Threshold voltage 2.14 V Dielectricanisotropy (Δε): 4.8 Birefringence index (Δn): 0.090

For the measurement of threshold voltage (Vth), the nematic liquidcrystal composition is packed into a TN cell having a thickness of 6 μm.The measurement is effected at a temperature of 20° C.

The physical properties of the nematic liquid crystal composition (M-3)and the electro-optical properties of the liquid crystal device preparedtherefrom are as follows:

T_(N-1): 120.0° C. T_(C-N): −2° C. Threshold voltage 2.06 V Dielectricanisotropy (Δε): 5.5 Birefringence index (Δn): 0.110

It can thus be seen that the addition of the compound (Ic-7) makes itpossible to raise the upper nematic phase temperature limit (T_(N-1)) bynot lower than 3°. The nematic liquid crystal composition (M-3) wascooled to a temperature of −60° C. to undergo crystallization. Thenematic liquid crystal composition (M-3) thus crystallized was thenmeasured for melting point (T_(C-N)). The results were −2° C.,demonstrating that the composition (M-3) exhibits a melting point dropof as much as 13° from the host liquid crystal composition (H).Accordingly, the stable temperature range of nematic phase can beexpanded by as much as about 16°. It can also be seen that theincorporation of the compound (Ic-7) makes it possible to increase thedielectric anisotropy of liquid crystal composition and lower thethreshold voltage of liquid crystal composition. The increase in thebirefringence index could be suppressed to 0.02 from that of the hostliquid crystal (H).

The liquid crystal device was then measured for voltage holding ratio atroom temperature and 80° C. The results were extremely good at any ofthe two temperature ranges, demonstrating that it can be sufficientlyused in active matrix driving.

A compound represented by the following general formula (R-1) having astructure similar to the compound (Ic-7) but having 1,4-phenylene groupinstead of 2,6-naphthylene group:

was added to the host liquid crystal composition (H) in the same amountas mentioned above (20%) to prepare a liquid crystal composition (HR-1).The upper nematic phase temperature limit (T_(N-1)) of the liquidcrystal composition (HR-1) was 101° C., which is far lower than that ofthe composition (M-3) as expected. The liquid crystal composition (HR-1)exhibited a melting point (T_(C-N)) of 5° C., which is higher than thatof the composition (M-3). Accordingly, the liquid crystal composition(HR-1) exhibited a nematic phase temperature range of as much as 25° ormore smaller than the composition (M-3).

It can thus be seen that the composition (M-3) exerts a better effectthan the conventional compounds to obtain a liquid crystal compositionhaving a wide operating temperature range, a low threshold voltage and aproper birefringence index.

The compound represented by the general formula (Id-1) set forth inTable 3:

was added to a host liquid crystal composition (H) having a wideoperating temperature range and a low viscosity in an amount of 20% byweight to prepare a liquid crystal composition (M-4).

The physical properties of the compound (Id-1) and the electro-opticalproperties of the liquid crystal device prepared therefrom are asfollows:

T_(N-1): 91.0° C. Threshold voltage (Vth) 1.94 V Dielectric anisotropy(Δε): 4.85 Response (τr = τd): 28.4 m sec. Birefringence index (Δn):0.112

It can thus be seen that the incorporation of the compound (Id-1) in anamount of 20% causes a slight drop of the upper nematic phasetemperature limit (T_(N-1)) but makes it possible to lower the thresholdvoltage of the liquid crystal composition and drastically raise thebirefringence index of the liquid crystal composition (by about 0.02from that of the host liquid crystal composition (H)) withoutdrastically deteriorating the response. Subsequently, the liquid crystalcomposition was allowed to stand at room temperature for 1 month.However, no crystallization or phase separation were observed. It canthus be seen that the compound (Id-1) has an excellent miscibility withthe conventional liquid crystals. The liquid crystal composition (M-4)was cooled to a temperature of −15° C. to undergo crystallization, andthen measured for melting point (T_(C-N)). The results were 14° C.

On the other hand, a compound represented by the general formula (R-2)having a structure similar to that of the compound (Id-1) but having abiphenyl skeleton:

was added to the host liquid crystal composition (H) in the same amountas mentioned above (20% by weight) to prepare a liquid crystalcomposition (HR-2). The liquid crystal composition (HR-2) thus preparedwas then measured for physical properties and electro-optical propertiesin the same manner as mentioned above. The results are as follows:

T_(N-1): 86.0° C. Threshold voltage (Vth): 1.86 V Dielectric anisotropy(Δε): 4.92 Response (τr = τd): 27.0 m sec. Birefringence index (Δn):0.096

The comparison of the liquid crystal composition (HR-2) with the liquidcrystal composition (H-1) shows that the liquid crystal composition(HR-2) exhibits a slightly higher response and a slightly lowerthreshold voltage (Vth). However, the upper nematic phase temperaturelimit (T_(N-1)) of the liquid crystal composition (HR-2) showed afurther drop. The liquid crystal composition (HR-2) also showed only aslight increase in birefringence index.

Subsequently, the compound represented by the general formula (Id-2) setforth in Table 1:

was added to the liquid crystal composition (H) in the same amount asmentioned above (20%) to prepare a liquid crystal composition (M-5). Thephysical properties of the liquid crystal composition (M-5) and theelectro-optical properties of the liquid crystal device preparedtherefrom are as follows:

T_(N-1): 85.1° C. Threshold voltage (Vth): 1.74 V Dielectric anisotropy(Δε): 5.7 Response (τr = τd): 31.1 m sec. Birefringence index (Δn):0.107

The comparison of the liquid crystal composition (M-5) with the liquidcrystal composition (M-4) shows that the liquid crystal composition(M-5) exhibits a slightly lower T_(N-1) and a slightly reducedbirefringence index but has a quick response similarly to the liquidcrystal composition (M-4) and a further drop of threshold voltage.

The compound represented by the general formula (Id-7) set forth inTable 3:

exhibits a melting point of −16° C. and a nematic phase up to 13° C. Onthe contrary, the compound (Id-1) having a skeleton structure similar tothat of the compound (Id-7) but having naphthalene ring not substitutedby fluorine is a crystalline material having a melting point of 62.5° C.which shows no liquid-crystallinity. The liquid crystal compositionobtained by adding the liquid crystal composition (Id-1) to a widelyused host liquid crystal showed T_(N-1) of −12° C. Thus, the compound(Id-7) exhibits a better liquid-crystallinity.

It can thus be seen that the compound represented by the general formula(Id-7) causes no deterioration of liquid-crystallinity despite of thedrop of melting point due to the incorporation of fluorine innaphthalene ring.

The foregoing compound (Id-7) was added to the host liquid crystalcomposition (H) in an amount of 20% by weight to prepare a liquidcrystal composition (M-6).

T_(N-1): 86.0° C. T_(C-N): 12° C. Threshold voltage (Vth): 1.65 VDielectric anisotropy (Δε): 6.5 Birefringence index (Δn): 0.107 Response(τr = τd): 28.8 m sec.

The incorporation of the compound (Id-7) in an amount of 20% causes aslight drop of the upper nematic phase temperature limit (T_(N-1)) butcan provide a high speed response similarly to the host liquid crystalcomposition (H) and makes it possible to drastically lower the thresholdvoltage of the liquid crystal composition (by 0.3 V). Further, thebirefringence of the liquid crystal composition can be drasticallyincreased from the host liquid crystal composition (H).

The liquid crystal device was then measured for voltage holding ratio atroom temperature and 80° C. The results were good at any of the twotemperature ranges, demonstrating that the liquid crystal device can besufficiently used in active matrix driving.

It can thus be seen that the compound represented by the general formula(Id) of the present invention exerts a better effect than theconventional compounds to obtain a low viscosity, an excellent response,a large birefringence index, a wide nematic phase operating temperaturerange, and a low threshold voltage.

Accordingly, the compound (I), when used in admixture with other nematicliquid crystal compounds, can be preferably used as a liquid crystalmaterial for field effect type display call such as TN type and STN typedisplay cells, particularly liquid crystal material which can operate ata wide temperature range and can be driven at a low voltage. Further,the compound represented by the general formula (I) has no stronglypolar group in its molecule and thus can easily provide a large specificresistivity and a high voltage holding ratio. Thus, the compoundrepresented by the general formula (I) can also be used as a constituentof liquid crystal material for active matrix driving. The presentinvention provides a liquid crystal composition comprising as aconstituent at least one of the compounds represented by the generalformula (I) and a liquid crystal device comprising the liquid crystalcomposition.

Specific representative examples of the nematic liquid crystal compoundwhich can be used in admixture with the compound represented by thegeneral formula (I) include phenyl benzoate derivative, phenylcyclohexanecarboxylate derivative, biphenyl-4-yl cyclohexanecarboxylatederivative, phenyl cyclohexanecarbonyloxybenzoate derivative, phenylcyclohexanecarboxylate derivative, phenyl cyclohexylbenzoate derivative,cyclohexyl cyclohexylbenzoate derivative, biphenyl derivative,cyclohexylbenzene derivative, terphenyl derivative, bicyclohexanederivative, 4-cyclohexylbiphenyl derivative, 4-phenylbicyclohexanederivative, tercyclohexane derivative, 1,2-dicyclohexylethanederivative, 1,2-diphenylethane derivative, 1,2-diphenylethinederivative, (2-cyclohexylethyl)benzene derivative,4-phenethylbicyclohexane derivative, 4-(2-cyclohexylethyl)biphenylderivative, 1-(4-phenyl)cyclohexyl-2-cyclohexylethane derivative,1-(4-cyclohexylphenyl)-2-phenylethine derivative, phenylpyrimidinederivative, (4-biphenyl-4-yl)pyrimidine derivative, phenylpyridinederivative, and (4-biphenyl-4-yl)pyridine derivative. Particularlypreferred for active matrix drive among these derivatives are biphenylderivative, cyclohexylbenzene derivative, terphenyl derivative,bicyclohexane derivative, 4-cyclohexylbiphenyl derivative,4-phenylbicyclohexane derivative, tercyclohexane derivative,1,2-dicyclohexylethane derivative, 1,2-diphenylethane derivative,1,2-diphenylethine derivative, (2-cyclohexylethyl)benzene derivative,4-phenethylbicyclohexane derivative, 4-(2-cyclohexylethyl)biphenylderivative, 1-(4-phenyl)cyclohexyl-2-cyclohexylethane derivative, and1-(4-cyclohexylphenyl)-2-phenylethine derivative.

EXAMPLES

The present invention will be further described in the followingexamples, but the present invention should not be construed as beinglimited thereto.

The structure of compounds were identified by nuclear magnetic resonancespectrum (NMR), mass spectrum (MS) and infrared absorption spectrum(IR). The term “%” as used hereinafter is meant to indicate % by weight.

Example 1 Synthesis of2-(3,4-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene (1-a)Synthesis of 2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthalene

5.7 g of magnesium was suspended in 12 ml of tetrahydrofuran. To thesuspension was then added dropwise a solution of 50 g of6-bromo-2-methoxynaphthalone in 200 ml of tetrahydrofuran at a rate suchthat tetrahydrofuran was gently refluxed. The reaction mixture was thenfurther stirred for 1 hour. To the reaction solution was then addeddropwise a solution of 30 g of 4-propylcyclohexanene in 120 ml oftetrahydrofuran at room temperature. The reaction mixture was thenfurther stirred for 1 hour. To the reaction solution was then added 200ml of a 10% hydrochloric acid. The reaction mixture was extracted with300 ml of toluene, washed with water, saturated aqueous solution ofsodium bicarbonate and saturated brine, and then dried over anhydroussodium sulfate. The solvent was then distilled off. To the residue werethen added 280 ml of toluene and 4.0 g of p-toluenesulfonic acidmonohydrate. The reaction mixture was then heated under reflux for 3hours. The reaction solution was allowed to cool to room temperature,washed with water, saturated aqueous solution of sodium bicarbonate andsaturated brine, and then dried over anhydrous sodium sulfate. Thesolvent was then distilled off. The residue was then recrystallized fromethanol to obtain 44.8 g of2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthalene.

(1-b) Synthesis of 2-methoxy-6-(trans-4-propyloyclohexyl)naphthalene

44.8 g of 2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthalene wasdissolved in 800 ml of ethyl acetate. To the solution was then added 10g of 5% palladium carbon. The reaction mixture was then stirred at ahydrogen pressure of 4 kg/cm² for 6 hours. The catalyst was then removedby filtration. The solvent was then distilled off. The residue was thendissolved in 180 ml of N,N-dimethylformamide. To the solution was thenadded 18 g of potassium t-butoxide. The reaction mixture was then heatedto a temperature of 120° C. with stirring for 1 hour. The reactionsolution was then allowed to cool to room temperature. To the reactionsolution was then added 70 ml of a 10% hydrochloric acid to causescrystallization. The crystal thus precipitated was filtered off, washedwith water, and then dried under reduced pressure. The crystal was thenrecrystallized from ethanol to obtain 28.0 g of2-methoxy-6-(trans-4-propylcyclohexyl)naphthalene.

(1-c) Synthesis of 6-(trans-4-propylcyclohexyl)-2-naphthol

To 28.0 g of 2-methoxy-6-(trans-4-propylcyclohexyl)naphthalene wereadded 280 ml of acetic acid and 280 ml of 48% hydxobromic acid. Thereaction mixture was then heated under reflux for 12 hours. The reactionsolution was then allowed to cool to room temperature. To the reactionsolution was then added 500 ml of water to cause crystallization. Thecrystal thus precipitated was then filtered off. The crystal was washedwith water, and then dried under reduced pressure to obtain 26.8 g of6-(trans-4-propylcyclohexyl)-2-naphthol.

(1-d) Synthesis of 6-(trans-4-propylcyclohexyl)naphthalene-2-yltrifluoromethanesulfonate

To 25.0 g of 6-(trans-4-propylcyclohexyl)-2-naphthol were added 100 mlof dichloromethane and 30 g of trifluoromethanesulfonic anhydride. Thereaction mixture was then cooled to a temperature of 5° C. To thereaction mixture was then added a solution of 11.0 g of pyridine in 40ml of dichloromethane at a rate such that the resulting temperaturedidn't exceed 20° C. After the termination of dropwise addition, thereaction mixture was returned to room temperature with stirring. To thereaction mixture was then added 150 ml of water. The resulting organicphase was washed with water and saturated brine, and then dried overanhydrous sodium sulfate. The solvent was then distilled off. Theresidue was then purified through silica gel column chromatography(solvent: dichloromethane) to obtain 36.7 g of6-(trans-4-propylcyclohexyl)naphthalene-2-yl trifluoromethane sulfonate.

(1-e) Synthesis of2-(3,4-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene

1.0 g of magnesium was suspended in 2 ml of tetrahydrofuran. To thesuspension was then added dropwise a solution of 7.0 g of3,4-difluoro-1-bromobenzene in 35 ml of tetrahydrofuran at a rate suchthat tetrahydrofuran was gently refluxed. The reaction mixture was thenfurther stirred at room temperature for 1 hour. Excessive magnesium wasremoved by filtration. The reaction solution was then added dropwise toa solution of 10.0 g of 6-(trans-4-propylcyclohexyl)naphthalene-2-yltrifluoromethane sulfonate and 0.3 g oftetrakis(triphenylphosphine)palladium in 50 ml of tetrahydrofuran atroom temperature. The reaction mixture was then stirred at roomtemperature for 1 hour. To the reaction mixture was then added 100 ml ofwater. The reaction mixture was extracted with 200 ml of toluene, washedwith water and saturated brine, and then dried over anhydrous sodiumsulfate. The solvent was then distilled off. The residue was purifiedthrough silica gel column chromatography (hexane), and thenrecrystallized from ethanol to obtain 7.1 g of a purified material. (Cr90 N 200.5 I)

The following compounds were similarly obtained.

-   2-(3,4-Difluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   2-(3,4-Difluorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   2-(3,4-Difluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   2-(3,4,5-Trifluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   2-(3,4,5-Trifluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   2-(3,4,5-Trifluorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   2-(3,4,5-Trifluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene

Example 2 Synthesis of2-(3,4,5-trifluorophenyl)-6-[2-(trans-4-propyloyclohexyl)ethyl]naphthalene(2-a) Synthesis of 6-(3,4,5-trifluorophenyl)naphthalene-2-yltrifluoromethanesulfonate

To 25.0 g of 6-(3,4,5-trifluorophenyl)-2-hydroxynaphthalene were added200 ml of dichloromethane and 34.0 g of trifluoromethanesulfonicanhydride. The reaction mixture was then cooled to a temperature of 5°C. To the reaction mixture was then added a solution of 12.0 g ofpyridine in 48 ml of dichloromethane at a rate such that the resultingtemperature didn't exceed 20° C. After the termination of dropwiseaddition, the reaction mixture was returned to room temperature withstirring. To the reaction mixture was then added 200 ml of water. Theresulting organic phase was washed with water and saturated brine, andthen dried over anhydrous sodium sulfate. The solvent was then distilledoff. The residue was then purified through silica gel columnchromatography (dichloromethane) to obtain 37.3 g of6-(3,4,5-trifluorophenyl)naphthalene-2-yl trifluoromethanesulfonate.

(2-b) Synthesis of2-(trans-4-propylcyclohexyl)ethynyl-6-(3,4,5-trifluorophenyl)naphthalene

25.0 g of 6-(3,4,5-trifluorophenyl)naphthalene-2-yltrifluoromethanesulfonate and 1-ethynyl-4-propylcyclohexane weredissolved in a mixture of 125 ml of N,N-dimethylformamide and 25 ml oftriethylamine. To the solution were then added 0.7 g oftetrakis(triphenylphosphine)palladium and 0.2 g of copper iodide (I).The reaction mixture was then stirred at a temperature of 50° C. for 3hours. The reaction solution was then allowed to cool to roomtemperature. To the reaction solution was then added 150 ml of water.The reaction solution was extracted with 200 ml of toluene, washed withwater and saturated brine, and then dried over anhydrous sodium sulfate.The solvent was then distilled off. The residue was then recrystallizedfrom ethanol to obtain 17.6 g of2-(trans-4-propylcyclohexyl)ethynyl-6-(3,4,5-trifluorophenyl)naphthalene.

(2-c) Synthesis of2-(3,4,5-trifluorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene

17.6 g of2-(trans-4-propylcyclohexyl)ethynyl-6-(3,4,5-trifluorophenyl)naphthalenewas dissolved in 400 ml of tetrahydrofuran. To the solution was thenadded 5 g of 5% palladium carbon. The reaction mixture was then stirredat a hydrogen pressure of 5 kg/cm² for 6 hours. The catalyst was thenremoved by filtration. The solvent was then distilled off. The residuewas purified through silica gel column chromatography (hexane), and thenrecrystallized from ethanol to obtain 11.5 g of a purified product. (Cr62 N 134 I)

The following compounds were prepared in the same manner as mentionedabove.

-   2-(3,4,5-Trifluorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   2-(3,4,5-Trifluorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   2-(3,4,5-Trifluorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   2-(3,4-Difluorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   2-(3,4-Difluorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene    Cr 110 N 166 I-   2-(3,4-Difluorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   2-(3,4-Difluorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene

Example 3 Synthesis of2-(3,4-difluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene

The Grignard reaction of Example (1-a) was followed except that1,4-cyclohexadione monoethylene acetal was used instead of4-propylcyclohexanene. The reaction product was then dehydrated withpotassium hydrogensulfate. To the toluene solution was then addedethylene glycol. The reaction mixture was then heated under reflux whilethe azeotropically distilled water was being driven out of the system.The reaction solution was allowed to cool to room temperature, washedsequentially with water, saturated aqueous solution of sodiumbicarbonate and saturated brine, and then dehydrated and dried overanhydrous sodium sulfate. The solvent was then distilled off to obtain4-(6-methoxynaphthalene-2-yl)-3-cyclohexenone ethylene acetal. Theproduct was dissolved in toluene, and then subjected to catalyticreduction in the same manner as (1-b). To the reaction solution was thenadded formic acid. The reaction mixture was heated with stirring, andthen cooled. To the reaction solution was then added water. Theresulting toluene phase was then washed. The solvent was then distilledoff. The resulting crude crystal was then recrystallized from ethanol toobtain 4-(6-methoxy naphthalene-2-yl)cyclohexanene in crystal form. Thecrystal thus obtained was dissolved in a mixture of toluene and THF, andthen cooled. To the reaction solution was then added a Wittig reagentprepared from methoxymethyltriphenylphosphonium bromide and potassiumt-butoxide. The reaction mixture was then returned to room temperature.To the reaction mixture were then added water and hexane. Insolublematters were then removed from the resulting hexane phase by filtration.The residue was then washed with a mixture of water and methanol. Thesolvent was then distilled off. The residue was then dissolved in THF.To the solution was then added diluted hydrochloric acid. The reactionsolution was heated under reflux for 1 hour, and then cooled. To thereaction solution was then added water. The reaction solution was thenextracted with ethyl acetate. The solvent was then distilled off. Theresidue was then dissolved in ethanol. To the solution was then added a20% aqueous solution of sodium hydroxide. The reaction mixture was thenstirred at room temperature. To the reaction solution was then addedwater. The reaction solution was extracted with toluene, washed, andthen dried. The solvent was then distilled off to obtaintrans-4-(6-methoxynaphthalene-2-yl)cyclohexanecarbaldehyde in crystalform. The crystal thus obtained was dissolved in THF. To the reactionsolution was then added a Wittig reagent prepared frommethyltriphanylphosphonium iodide and potassium t-butoxide. The reactionmixture was then returned to room temperature. To the reaction mixturewere then added water and hexane. Insoluble matters were then removedfrom the resulting hexane phase by filtration. The residue was washedwith a mixture of water and methanol, and then dried. The solvent wasthen distilled off. The residue was then purified through silica gelcolumn chromatography (toluene) to obtain2-(trans-4-vinylcyclohexyl)-6-methoxynaphthalene in crystal form. Thecrystal was then processed in the same manner as (1-c), (1-d) and (1-e)to obtain the titled2-(3,4-difluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene.

The following compounds were prepared in the same manner as mentionedabove.

-   2-(3,4-Difluorophenyl)-6-[trans-4-(3-butenyl)cyclohexyl]naphthalene-   2-(3,4,5-Trifluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   2-(3,4,5-Trifluorophenyl)-6-[trans-4-(3-butenyl)cyclohexyl]naphthalene

Example 4 Synthesis of1-fluoro-2-(3,4-difluorophenyl)-6-propylnaphthalene (4-a) Synthesis of2-methoxy-6-propylnaphthalene

To a solution of 200 g of 2-bromo-6-methoxynaphthalene and 2.5 g ofdichloro[1,2-bis(diphenylphosphino)ethane] nickel (II) in 200 ml oftetrahydrofuran (THF) was added dropwise a Grignard reagent preparedfrom 125 g of propyl bromide and 27 g of magnesium under nitrogenatomsphere. The reaction mixture was further stirred for 1 hour, andthen poured into water. To the reaction mixture was then added dilutedhydrochloric acid. The resulting organic phase was then separated. Theresulting aqueous phase was extracted with toluene. The organic phaseand the material thus extracted were together washed sequentially withwater, saturated aqueous solution of sodium bicarbonate, water andsaturated brine, and then dehydrated and dried over anhydrous sodiumsulfate. The solvent was then distilled off to obtain 172 g of2-methoxy-6-propylnaphthalene.

(4-b) Synthesis of 6-propyl-2-naphthol

The total amount (172 g) of 2-methoxy-6-propylnaphthalene obtained inthe process (4-a) was added to a mixture of 680 ml of acetic acid and680 ml of a 48% hydrobromic acid. The reaction mixture was heated underreflux for 8 hours. The reaction solution was then allowed to cool toroom temperature. To the reaction solution was then added 1,300 ml ofwater. The resulting crystal was filtered off, and then washed withwater. The resulting crystal was dissolved in 1,000 ml of ethyl acetate,and then washed sequentially with water, saturated aqueous solution ofsodium bicarbonate, water and saturated brine. The product was thendehydrated and dried over anhydrous sodium sulfate. The solvent was thendistilled off to obtain 152 g of 6-propyl-2-naphthol in the form ofcrude crystal form.

(4-c) Synthesis of 1-fluoro-6-propyl-2-naphthol

To a solution of 20 g of 6-propyl-2-naphthol and 1.8 g of sodiumtrifluoromethanesulfonate in 80 ml of dichloromethane was added 23.7 gof N,N′-difluoro-2,21′-dipyridinium bistetrafluoroborate. The reactionmixture was then stirred for 8 hours. The reaction solution was thenpoured in water. To the reaction mixture was then added dilutedhydrochloric acid. The resulting organic phase was then separated. Theresulting aqueous phase was extracted with toluene. The organic phaseand the material thus extracted were together washed sequentially withwater and saturated brine, and then dehydrated and dried over anhydroussodium sulfate. The solvent was distilled off to obtain an oily matterwhich was then purified through silica gel column chromatography(hexane/ethyl acetate=9/1) to obtain 17.1 g of1-fluoro-6-propyl-2-naphthol.

(4-d) Synthesis of 1-fluoro-6-propylnaphthalene-2-yltrifluoromethanesulfonate

The total amount (17.1 g) of 1-fluoro-6-propyl-2-naphthol obtained inthe process (4-c) and 25.1 g of trifluoromethanesulfonic anhydride weredissolved in 80 ml of dichloromethane. To the solution was then addeddropwise 15.9 ml of pyridine. The reaction mixture was then furtherstirred for 1 hour. To the reaction solution was then added dilutedhydrochloric acid. The resulting organic phase was separated. Theresulting aqueous phase was then extracted with toluene. The organicphase and the material thus extracted were washed sequentially withwater and saturated brine, and then dehydrated and dried over anhydroussodium sulfate. The solvent was distilled off to obtain a crystal whichwas then purified though silica gel column chromatography to obtain 24.2g of 1-fluoro-6-propylnaphthalene-2-yl trifluoromethanesulfonate.

(4-e) Synthesis of 1-fluoro-2-(3,4-difluorophenyl)-6-propyl naphthalene

20 g of 1-fluoro-6-propylnaphthalene-2-yl trifluoromethanesulfonateobtained in the process (4-d) and dibromobis(triphenylphosphine)nickel(II) were dissolved in 80 ml of THF. To the solution was added dropwisea Grignard reagent prepared from 25.8 g of 3,4-difluorobromobenzene and3.2 g of magnesium under a nitrogen atomsphere. The reaction mixture wasfurther stirred for 1 hour. To the reaction solution was then addeddiluted hydrochloric acid. The resulting organic phase was thenseparated. The resulting aqueous phase was then extracted with toluene.The organic phase and the material thus extracted were together washedsequentially with water, saturated aqueous solution of sodiumbicarbonate and saturated brine, and then dehydrated and dried overanhydrous sodium sulfate. The solvent was then distilled off to obtain acrystal. The crystal thus obtained was purified through silica galcolumn chromatography (hexane), and then subjected to distillation toobtain 6.5 g of 1-fluoro-2-(3,4-difluorophenyl)-6-propylnaphthalene.Cr-16 N 13 I

The following compounds were prepared in the same manner as mentionedabove.

-   1-Fluoro-2-(3,4-difluorophenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-butylnaphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-propylnaphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-butylnaphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl-6-naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-ethylnaphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-propylnaphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-butylnaphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-pentylnaphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-hexylnaphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-heptylnaphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-propylnaphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-butylnaphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-propylnaphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-butylnaphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2- phenyl-6-ethylnaphthalene-   1-Fluoro-2-phenyl-6-propylnaphthalene-   1-Fluoro-2-phenyl-6-butylnaphthalene-   1-Fluoro-2-phenyl-6-pentylnaphthalene-   1-Fluoro-2-phenyl-6-hexylnaphthalene-   1-Fluoro-2-phenyl-6-heptylnaphthalene-   1-Fluoro-2-phenyl-6-(3-butenyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-ethylnaphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-propylnaphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-butylnaphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-pentylnaphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-hexylnaphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-heptylnaphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-propylnaphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-butylnaphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-propylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-butylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-propylnaphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-butylnaphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-propylnaphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-butylnaphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-propylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-butylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-propylnaphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-butylnaphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-propylnaphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-butylnaphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-propylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-butylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-propylnaphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-butylnaphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-propylnaphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-butylnaphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenylphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-propylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-butylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenylphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-propylnaphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-butylnaphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-propylnaphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-butylnaphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-propylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-butylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-propylnaphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-butylnaphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-ethylnaphthalene-   1-Fluoro-2-(4-methylphenyl)-6-propylnaphthalene-   1-Fluoro-2-(4-methylphenyl)-6-butylnaphthalene-   1-Fluoro-2-(4-methylphenyl)-6-pentylnaphthalene-   1-Fluoro-2-(4-methylphenyl)-6-hexylnaphthalene-   1-Fluoro-2-(4-methylphenyl)-6-heptylnaphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3,4-difluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3,4-difluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3,4-difluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3,4-difluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3,4-difluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3,4-difluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3,4-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3,4,5-trifluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(4-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(4–3-fluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(4–3-fluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(4–3-fluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(4–3-fluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(4–3-fluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(4–3-fluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(4–3-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(4-chlorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(4-chlorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(4-chlorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(4-chlorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(4-trifluoromethylphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethyl    naphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(4-allyloxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(4-allyloxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(4-allyloxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(4-allyloxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(4-allyloxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(4-allyloxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(4-allyloxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(4-methylphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(4-methylphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(4-methylphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(4-methylphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(4-methylphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(4-methylphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(4-methylphenyl)-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-[4-(3-butenyl)phenyl]phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-(3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5difluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-allyloxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methylphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methylphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methylphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methylphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methylphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methylphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-methylphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-chlorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-chlorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-chlorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-chlorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   0-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethoxy    phenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxypheny1)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-allyloxyphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-allyloxyphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-allyloxyphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-allyloxyphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-allyloxyphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-allyloxyphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-allyloxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-methylphenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-(3-butenyl)naphthalene

Example 5 Synthesis of1-fluoro-2-(3,4-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene(5-a) Synthesis of 2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthalene

22.6 g of magnesium was suspended in 30 ml of THF. To the suspension wasthen added dropwise a solution of 20 g of 2-bromo-6-methoxynaphthalenein 100 ml of THF at a rate such that THF was gently refluxed in about 2hours. The reaction mixture was then further stirred for 1 hour. To thereaction solution was then added dropwise a solution of 130.1 g of4-propylcyclohexanene in 520 ml of THF in 1 hour. The reaction mixturewas further stirred for 2 hours. To the reaction solution was then added200 ml of a 10% hydrochloric acid. To the reaction mixture was thenadded 200 ml of hexane. The resulting organic phase was then separated.The resulting aqueous phase was then extracted with 100 ml of hexane. Tothe material thus extracted was then added the organic phase. Themixture was washed with water, saturated aqueous solution of sodiumbicarbonate and saturated brine, and then dried over anhydrous sodiumsulfate. The solvent was distilled off. To the residue were then added280 ml of toluene and 4.0 g of p-toluenesulfonic acid monohydrate. Thereaction mixture was then heated under reflux for 3 hours. The reactionsolution was allowed to cool to room temperature, washed with water,saturated aqueous solution of sodium bicarbonate and saturated brine,and then dried over anhydrous sodium sulfate. The solvent was thendistilled off to obtain 260 g of an oily cyclohexanol derivative. Thetotal amount of the cyclohexanol derivative thus obtained was thendissolved in 800 ml of toluene. To the solution was then added 16.1 g ofp-toluenesulfonic monohydrate. The reaction mixture was then heated to atemperature of 110° C. with stirring while the distilled water was beingremoved away. After the termination of distillation of water, thereaction solution was then returned to room temperature. To the reactionsolution was then added 300 ml of water. The resulting organic phase wasthen separated. The organic phase thus separated was washed withsaturated aqueous solution of sodium bicarbonate, water and saturatedbrine, and then dried over anhydrous sodium sulfate. The solvent wasthen distilled off to obtain 246 g of2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthalene in the for of anoily crude product.

(5-b) Synthesis of 2-methoxy-6-(trans-4-propylcyclohexyl)naphthalene

The total amount of2-methoxy-6-(4-propylcyclohexa-1-ene-1-yl)naphthalene obtained in theprocess (5-a) was dissolved in 1.2 l of ethyl acetate. To the solutionwas then added 47 g of 5% palladium/carbon (hydrous). The reactionmixture was then stirred in an autoclave at a hydrogen pressure of 4kg/cm². The reaction mixture was than stirred at room temperature for 5hours. The catalyst was then removed by filtration through Celite. Thesolvent was then distilled off to obtain 260 g of a trans/cis mixture of2-methoxy-6-(4-propylcyclohexyl)naphthalene. The total amount of theproduct was then dissolved in 1.3 l of N,N-dimethylformamide (DMF). Tothe solution was then added 125 g of potassium t-butoxide. The reactionmixture was then heated under reflux for 5 hours. The reaction solutionwas then allowed to cool to room temperature. To the reaction solutionwas then added 200 ml of water. The reaction solution was then extractedtwice with 200 ml of toluene. The material thus extracted and theorganic phase were together washed with diluted hydrochloric acid,saturated aqueous solution of sodium bicarbonate, water and saturatedbrine, and then dried over anhydrous sodium sulfate. The solvent wasdistilled off. The residue was purified through silica gel columnchromatography (toluene), and then recrystallized twice from ethanol toobtain 115 g of 2-methoxy-6-(trans-4-propylcyclohexyl)naphthalene in theform of white crystal.

(5-c) Synthesis of 6-(trans-4-propylcyclohexyl)-2-naphthol

To the total amount of 2-methoxy-6-(trans-4-propylcyclohexyl)naphthaleneobtained in the process (5-b) were added 700 ml of acetic acid and 700ml of a 48% hydrobromic acid. The reaction mixture was then heated underreflux for 20 hours. The reaction solution was then allowed to cool toroom temperature. To the reaction solute on was then added 200 ml ofwater. The reaction solution was then extracted twice with 400 ml oftoluene. The material thus extracted and the organic phase were togetherwashed with water and then with saturated brine, and then dehydrated anddried over anhydrous sodium sulfate. The solvent was then distilled offto obtain 109 g of 6-(trans-4-propylcyclohexyl)-2-naphthol in the formof white crystal.

(5-d) Synthesis of 1-fluoro-6-(trans-4-propylcyclohexyl)-2-naphthol

The total amount of 6-(trans-4-propylcyclohexyl)-2-naphthol obtained inthe process (5-c) was dissolved in 500 ml of dichloromethane. To thesolution was then added 7 g of sodium trifluoromethanesulfonate. Thereaction mixture was then vigorously stirred. To the reaction solutionwas then added gradually 86.7 g of N,N′-difluoro-2,2′-dipyridiniumbistetrafluoroborate. The reaction mixture was then further stirred atroom temperature for 5 hours. To the reaction solution were added waterand then a 10% aqueous solution of sodium hydroxide so that excessfluorinating agent was decomposed. The reaction solution was thenreturned to acidity with diluted hydrochloric acid. The resultingorganic phase was then separated. The resulting aqueous phase was thenextracted with 100 ml of anhydrous sodium sulfate. The material thusextracted and the organic phase were together washed with water and thenwith saturated brine, and then dehydrated and dried over sodium sulfate.The solvent was distilled off to obtain 131.5 g of a crude crystal whichwas then purified through silica gel column chromatography (toluene) toobtain 83 g of 1-fluoro-6-(trans-4-proopylcyclohexyl)-2-naphthol in thetorn of white crystal

(5-e) Synthesis of 6-(trans-4-propylcyclohexyl)naphthalene-2-yltrifluoromethanesulfonate

The total amount of 1-fluoro-6-(trans-4-propylcyclohexyl)-2-naphtholobtained in the process (5-d) was dissolved in 450 ml ofdichloromethane. To the solution was added 55.3 ml oftrifluoromethanesulfonic anhydride to make a suspension which was thencooled to a temperature of 5° C. To the suspension was then addeddropwise 54 ml of pyridine with vigorous stirring. The reaction mixturewas then further stirred for 1 hour. To the reaction mixture was thenadded 100 ml of water to terminate the reaction. The resulting organicphase was then separated. The resulting aqueous phase was then extractedwith 100 ml of dichloromethane. The material thus extracted and theorganic phase were together washed sequentially with dilutedhydrochloric acid, saturated aqueous solution of sodium bicarbonate,water and saturated brine, and then dehydrated and dried over anhydroussodium sulfate. The solvent was distilled off to obtain 105 g of a crudecrystal which was then purified through silica gel column chromatography(hexane) to obtain 96 g of 6-(trans-4-propylcyclohexyl)naphthalene-2-yltrifluoromethanesulfonate in the form of white crystal.

(5-f) Synthesis of1-fluoro-2-(3,4-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene

1 g of magnesium was suspended in 1 ml of THF. To the suspension wasthen added dropwise a solution of 7.9 g of 3,4-difluoro-1-bromobenzenein 32 ml of THF at a rate such that THF was gently refluxed. Thereaction mixture was then stirred at room temperature for 1 hour. Excessmagnesium was then removed by filtration. The residue was then addeddropwise to a solution of 10 g of6-(trans-4-propylcyclohexyl)naphthalene-2-yl trifluoromethanesulfonateobtained in the process (2-e) and 0.5 g ofdibromobis(triphenylphosphine)nickel (II) in 40 ml of THF at atemperature of 40° C. The reaction mixture was then stirred for 1 hour.To the reaction mixture was then added 50 ml of water. The reactionmixture was extracted with 50 ml of toluene, washed with water andsaturated brine, and then dried over anhydrous sodium sulfate. Thesolvent was then distilled off. The residue was purified through silicagel column chromatography (hexane), and then recrystallized from ethanolto obtain 2.6 g of purified1-fluoro-2-(3,4-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene.(Cr 85 N 198.5 I)

The following compounds were prepared in the same manner as mentionedabove.

-   1-Fluoro-2-(3,4-difluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-phenyl-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-phenyl-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-phenyl-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-phenyl-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-phenyl-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-phenyl-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(trans-4-heptylcyclohexyl)naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(trans-4-propylcyclohexyl)naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(4-(3-butenyl)phenyl]-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(trans-4-heptylcyclohexyl)naphthalene

Example 6 Synthesis of1-fluoro-2-(3,4-difluorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene

The procedure of Example 5 was followed except thattrans-4-propylcyclohexane ethanol was used instead of4-propylcyclohexanene and isomerization in the process (5-b) was noteffected to obtain1-fluoro-2-(3,4-difluorophenyl)-6-[2-(trans-4-propylcyclohexylethyl]naphthalenein the form of white crystal.

The following compounds were prepared in the same manner as mentionedabove.

-   1-Fluoro-2-(3,4-difluorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-phenyl-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-phenyl-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-phenyl-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-phenyl-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-phenyl-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-phenyl-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-    cyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(trans-4-ethylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(trans-4-butylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(trans-4-hexylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-phenyl-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-phenyl-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-phenyl-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-phenyl-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-phenyl-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-phenyl-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene

0-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene

-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-[2-(4-heptylphenyl)ethyl]naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(4-ethylphenyl)ethyl]naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(4-propylphenyl)ethyl]naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(4-butylphenyl)ethyl]naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(4-pentylphenyl)ethyl]naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(4-hexylphenyl)ethyl]naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[2-(4-heptylphenyl)ethyl]naphthalene

Example 7 Synthesis of1-fluoro-2-(3,4,5-trifluorophenyl)-6-(4-propylphenyl)naphthaleneSynthesis of 6-(4-propylphenyl)-2-naphthol

50 g of 6-bromo-2-naphthol and 48 g of 4-propylphenylboric acid(synthesized by reacting a Grignard reagent prepared from4-propylbromobenzene with trimethyl borate, and then subjecting thereaction product to hydrolysis with hydrochloric acid) were dissolved ina mixture of 200 ml of toluene and 100 ml of ethanol. To the solutionwas then added 200 ml of a 2 N aqueous solution of potassium carbonate.To the reaction mixture was then added 2.6 g oftetrakis(triphenylphophine)palladium (0). The reaction mixture was thenheated under reflux for 6 hours. The reaction solution was then allowedto cool to room temperature. The resulting organic phase was thenseparated. The resulting aqueous phase was then extracted with toluene.The material thus extracted and the organic phase were together washedsequentially with diluted hydrochloric acid, water and saturated brine,and then dehydrated and dried over anhydrous sodium sulfate. The solventwas then distilled off to obtain 47 g of 6-(4-propylphenyl)-2-naphtholin crystal form.

The crystal thus obtained was then processed in the same manner as (5-d)and (5-e) to obtain1-fluoro-2-(3,4,5-trifluorophenyl)-6-(4-propylphenyl)naphthalene in theform of white crystal.

The following compounds were prepared in the same manner as mentionedabove.

-   1-Fluoro-2-(3,4-difluorophenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3,4-difluorophenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-phenyl-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-phenyl-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-phenyl-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-phenyl-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-phenyl-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-phenyl-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-phenyl-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenylphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenylphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-[4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(4-ethylphenyl)naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(4-propylphenyl)naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(4-butylphenyl)naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(4-hexylphenyl)naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-[4-(3-butenyl)phenyl]naphthalene

Example 8 Synthesis of1-fluoro-2-(3,4-difluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene

The Grignard reaction of Example 5 was followed except that1,4-cyclohexadione monoethylene acetal was used instead of4-propylcyclohexanene. The reaction product was then dehydrated withpotassium hydrogensulfate instead of p-toluenesulfonic acid. To thetoluene solution was then added ethylene glycol. The reaction mixturewas then heated under reflux while the azeotropically distilled waterwas being driven out of the system. The reaction solution was allowed tocool to room temperature, washed sequentially with water, saturatedaqueous solution of sodium bicarbonate and saturated brine, and thendehydrated and dried over anhydrous sodium sulfate. The solvent was thendistilled off to obtain 4-(6-methoxynaphthalene-2-yl)-3-cyclohexenoneethylene acetal. The product was dissolved in toluene, and thensubjected to catalytic reduction in the same manner as (2-b). To thereaction solution was than added formic acid. The reaction mixture washeated with stirring, and then cooled. To the reaction solution was thenadded water. The resulting toluene phase was then washed. The solventwas then distilled off. The resulting crude crystal was thenrecrystallized from ethanol to obtain 4-(6-methoxynaphthalene-2-yl)cyclohexanene in crystal form. The crystal thusobtained was dissolved in a mixture of toluene and THF, and then cooled.To the reaction solution was then added a Wittig reagent prepared frommethoxymethyltriphenylphosphonium bromide and potassium t-butoxide. Thereaction mixture was then returned to room temperature. To the reactionmixture were then added water and hexane. Insoluble matters were thenremoved from the resulting hexane phase by filtration. The residue wasthen washed with a mixture of water and methanol. The solvent was thendistilled off. The residue was then dissolved in THF. To the solutionwas then added diluted hydrochloric acid. The reaction solution washeated under reflux for 1 hour, and then cooled. To the reactionsolution was then added water. The reaction solution was then extractedwith ethyl acetate. The solvent was then distilled off. The residue wasthen dissolved in ethanol. To the solution was then added a 20% aqueoussolution of sodium hydroxide. The reaction mixture was then stirred atroom temperature. To the reaction solution was then added water. Thereaction solution was extracted with toluene, washed, and then dried.The solvent was then distilled off to obtaintrans-4-(6-methoxynaphthalene-2-yl)cyclohexane carbaldehyde in crystalform. The crystal thus obtained was dissolved in THF. To the reactionsolution was then added a Wittig reagent prepared frommethyltriphenylphosphonium iodide and potassium t-butoxide. The reactionmixture was then returned to room temperature. To the reaction mixturewere then added water and hexane. Insoluble matters were then removedfrom the resulting hexane phase by filtration. The residue was washedwith a mixture of water and methanol, and then dried. The solvent wasthen distilled off. The residue was then purified through silica gelcolumn chromatography (toluene) to obtain2-(trans-4-vinylcyclohexyl)-6-methoxynaphthalene in crystal form. Thecrystal was then processed in the same manner as (5-c), (5-d) and (5-e)to obtain the titled2-(3,4-difluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene.

The following compounds were prepared in the same manner as mentionedabove.

-   1-Fluoro-2-(3,4,5-trifluorophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(4-fluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-phenyl-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(4-chlorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-chlorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-chlorophenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(4-difluoromethoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-difluoromethoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-difluoromethoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(4-trifluoromethylphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-trifluoromethylphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-trifluoromethylphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-methoxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(4-allyloxyphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-(4-methylphenyl)-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-[4-(3-butenyl)phenyl]-6-(trans-4-vinylcyclohexyl)naphthalene

Example 9 Synthesis of1-fluoro-2-(4-cyanophenyl)-6-(trans-4-propylcyclohexyl)naphthalene

1-Fluoro-2-[4-(4,4-dimethyl-1,3-oxazolidine-2-yl)phenyl]-6-(trans-4-propylcyclohexyl)naphthalene(obtained in the same manner as (5-f) except that2-(4-bromophenyl)-4,4-dimethyl-1,3-oxazolidine was used instead of3,4-difluoro-1-bromobenzene) was dissolved in 50 ml of pyridine. To thesolution was then added dropwise 5.6 g of phosphorus oxychloride at atemperature of 25° C. The reaction mixture was then stirred at atemperature of 110° C. for 5 hours. Excess phosphorus oxychloride wasthen distilled off under reduced pressure. To the residue was then addeddiluted hydrochloric acid. The resulting aqueous phase was thenextracted with toluene. The material thus extracted and the organicphase were together washed with water, saturated aqueous solution ofsodium bicarbonate and saturated brine, and then dehydrated and driedover anhydrous sodium sulfate. The solvent was then distilled off. Theresidue was purified through silica gel column chromatography (hexane),and then recrystallized from ethanol to obtain 4.4 g of the titledcompound.

The following compounds were prepared in the same manner as mentionedabove.

-   1-Fluoro-2-(4-cyanophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(4-cyanophenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(4-cyanophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(4-cyanophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(4-cyanophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene

Example 10 Synthesis of1-fluoro-2-(3-fluoro-4-cyanophenyl)-6-(trans-4-propylcyclohexyl)naphthalene(10-a)1-Fluoro-2-(3-fluoro-4-trifluoromethanesulfonyloxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene

20 g of1-fluoro-2(3-fluoro-4-hydroxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene(obtained in the same manner as in (5-f) except that1-bromo-3-fluoro-4-methoxybenzene was used instead of3,4-difluoro-1-bromobenzene to obtain1-fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalenewhich was then demethylated with hydrobromic acid) was dissolved in 80ml of dichloromethane. To the solution was then added dropwise 15.8 g oftrifluoromethanesulfonic anhydride under cooling with ice. To thereaction mixture was then added dropwise 10 ml of pyridine in such amanner that the temperature thereof didn't exceed 5° C. After thetermination of dropwise addition, the reaction mixture was stirred atthe same temperature for 1 hour. To the reaction mixture was then added20 ml of water to terminate the reaction. The resulting organic phasewas washed twice with 20 ml of water, and then dehydrated and dried overanhydrous sodium sulfate. Subsequently, the solvent was distilled off.The residue was then purified through silica gel column chromatography(hexane) to obtain 24.3 g of1-fluoro-2-(3-fluoro-4-trifluoromethanesulfonyloxyphenyl)-6-(trans-4-propylcyclohexyl)naphthalene.

(10-b) Synthesis of1-fluoro-2-(3-fluoro-4-cyanophenyl)-6-(trans-4-propylcyclohexyl)naphthalene

The total amount of1-fluoro-2-(3-fluoro-4-trifluoromethanesulfonyloxyphenyl)-6-(trans-4-propylcyclohexyl)naphthaleneobtained in the process (10-a) was dissolved in 100 ml of acetonitrile.To the solution were then added 1.2 g ofdibromobis(triphenylphosphine)nickel (II), 1 g of triphenyl phosphine,0.25 g of zinc powder and 6.2 g of potassium cyanide. The reactionmixture was then heated to a temperature of 80° C. with stirring for 16hours. To the reaction solution was then added 20 ml of water toterminate the reaction. The resulting organic phase was washed twicewith 20 ml of water, and then dehydrated and dried over anhydrous sodiumsulfate. The product was purified through silica gel columnchromatography (hexane/dichloromethane=6/4), and then recrystallizedfrom ethanol to obtain 14.6 g of5-fluoro-6-cyano-2-(trans-4-propylcyclohexyl)naphthalene.

The following compounds were prepared in the same manner as mentionedabove.

-   5-fluoro-6-cyano-2-(trans-4-ethylcyclohexyl)naphthalene-   5-fluoro-6-cyano-2-(trans-4-butylcyclohexyl)naphthalene-   5-fluoro-6-cyano-2-(trans-4-pentylcyclohexyl)naphthalene-   5-fluoro-6-cyano-2-(trans-4-hexylcyclohexyl)naphthalene-   5-fluoro-6-cyano-2-(trans-4-heptylcyclohexyl)naphthalene

Example 11 Synthesis of1-fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-(trans-4-propylcyclohexyl)naphthalene

10 g of2-(4-carbamoyl-3,5-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthalene(synthesized by lithioating1-fluoro-2-(3,5-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthaleneobtained in Example 5 with butyl lithium, blowing carbon dioxide throughthe material to produce benzoic acid, reacting the product with thionylchloride to produce acid chloride, and then blowing ammonia gas throughthe material) was dissolved in 40 ml of DMF. To the solution was thenadded 2.5 ml of phosphorus oxychloride. The reaction mixture was thenallowed to undergo reaction at a temperature of 25° C. for 2 hours. Thereaction solution was then poured into ice water. To the reactionsolution was then added diluted hydrochloric acid. The resulting aqueousphase was then extracted with toluene. The material thus extracted andthe organic phase were together washed with water, saturated aqueoussolution of sodium bicarbonate and saturated brine, and then dehydratedand dried over anhydrous sodium sulfate. The residue was purifiedthrough silica gel column chromatography (hexane/dichloromethane=6/4),and then recrystallized from ethanol to obtain 7.4 g of1-fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-(trans-4-propylcyclohexyl)naphthalene.

The following compounds were prepared in the same manner as mentionedabove.

-   1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-(trans-4-ethylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-(trans-4-hexylcyclohexyl)naphthalene-   1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-(trans-4-heptylcyclohexyl)naphthalene

Example 12 Synthesis of 2-(3,4-difluorophenyl)-6-propylnaphthalene(12-a) Synthesis of 6-(3,4-difluorophenyl)-2-naphthol

To 25.0 g of 6-bromo-2-naphthol and 22.0 g of 3,4-difluorophenylboricacid were added 100 ml of toluene, 50 ml of ethanol, 50 ml of a 2 Naqueous solution of potassium carbonate and 1.3 g oftetrakis(triphenylphosphine)palladium (0). The reaction mixture washeated under reflux for 3 hours. The reaction solution was then allowedto cool to room temperature. The resulting organic phase was separated,washed with water and saturated brine, and then dried over anhydroussodium sulfate. The solvent was then distilled off. The residue waspurified through silica gel column chromatography (dichloromethane) toobtain 25.3 g of 6-(3,4-difluorophenyl)-2-naphthol.

(12-b) Synthesis of 6-(3,4-difluorophenyl)-2-naphthyltrifluoromethanesulfonate

7.6 g of 6-(3,4-difluorophenyl)-2-naphthol was dissolved in 30 ml ofpyridine. The solution was then cooled to a temperature of not higherthan 10° C. with ice. To the reaction solution was then added dropwise10.0 g of trifluoromethanesulfonic anhydride at a rate such that thetemperature thereof was kept at 10° C. with stirring. The reactionsolution was then returned to room temperature. The reaction solutionwas then stirred for 1 hour. To the reaction solution was then added 50ml of water. The reaction solution was extracted with 100 ml ofdichloromethane, washed with water and saturated brine, and then driedover anhydrous sodium sulfate. The solvent was then distilled off toobtain 11.4 g of 6-(3,4-difluorophenyl)-2-naphthyltrifluoromethanesulfonate.

(12-c) Synthesis of 2-(3,4-difluorophenyl)-6-(1-propynyl)naphthalene

11.4 g of 6-(3,4-difluorophenyl)-2-naphthyl trifluoromethanesulfonateand 60 ml of DMF were dissolved in 20 ml of triethylamine. To thesolution were then added 0.4 g of tetrakis(triphenylphosphine)palladium(0) and 0.1 g of copper iodide (I). Methyl acetylene was then introducedinto the reaction mixture at ordinary temperature and pressure. Thereaction mixture was then stirred for 2 hours. The reaction solution wasneutralized with a 10% hydrochloric acid, extracted with 100 ml oftoluene, and then washed with water and saturated brine. The solvent wasthen distilled off. The residue was then purified through silica gelcolumn chromatography (hexane) to obtain 7.4 g of2-(3,4-difluorophenyl)-6-(1-propinyl)naphthalene.

(12-d) Synthesis of 2-(3,4-difluorophenyl)-6-propylnaphthalene

7.4 g of 2-(3,4-difluorophenyl)-6-(1-propynyl)naphthalene was dissolvedin 80 ml of ethyl acetate. To the solution was then added 1.5 g of 5%palladium carbon. Hydrogen was then introduced into the reaction mixtureat ordinary temperature and pressure. The reaction mixture was thenstirred for 6 hours. The catalyst was then removed by filtration. Thesolvent was then distilled off to obtain 7.2 g of2-(3,4-difluorophenyl)-6-propylnaphthalene. The product was thenrecrystallized from methanol to obtain 4.2 g of a purified product. (Cr62.5 I)

Example 13 Synthesis of 2-(3,4,5-trifluorophenyl)-6-propylnaphthalene

The procedure of Example 12 was followed except that3,4,5-trifluorophenylboric acid was used instead of3,4-difluorophenylboric acid to prepare 7 g of2-(3,4,5-trifluorophenyl)-6-propyl naphthalene from 7 g of6-bromo-2-naphthol. (Cr 50 I)

The following compounds were prepared in the same manner as Examples 12and 13.

-   2-(3,4-Difluorophenyl)-6-ethylnaphthalene-   2-(3,4-Difluorophenyl)-6-butylnaphthalene-   2-(3,4-Difluorophenyl)-6pentylnaphthalene-   2-(3,4-Difluorophenyl)-6-hexylnaphthalene-   2-(3,4-Difluorophenyl)-6-heptylnaphthalene-   2-(3,4-Difluorophenyl)-6-(3-butenyl)naphthalene-   2-(3,4,5-Trifluorophenyl)-6-ethylnaphthalene-   2-(3,4,5-Trifluorophenyl)-6-propylnaphthalene-   2-(3,4,5-Trifluorophenyl)-6-butylnaphthalene-   2-(3,4,5-Trifluorophenyl)-6-pentylnaphthalene-   2-(3,4,5-Trifluorophenyl)-6-hexylnaphthalene-   2-(3,4,5-Trifluorophenyl)-6-heptylnaphthalene-   2-(3,4,5-Trifluorophenyl)-6-(3-butenyl)naphthalene-   2-(4-Fluorophenyl)-6-ethylnaphthalene-   2-(4-Fluorophenyl)-6-propylnaphthalene-   2-(4-Fluorophenyl)-6-butylnaphthalene-   2-(4-Fluorophenyl)-6-pentylnaphthalene-   2-(4-Fluorophenyl)-6-hexylnaphthalene-   2-(4-Fluorophenyl)-6-heptylnaphthalene-   2-(4-Fluorophenyl)-6-(3-butenyl)naphthalene-   2-(3-Fluorophenyl)-6-ethylnaphthalene-   2-(3-Fluorophenyl)-6-propylnaphthalene-   2-(3-Fluorophenyl)-6-butylnaphthalene-   2-(3-Fluorophenyl)-6-pentylnaphthalene-   2-(3-Fluorophenyl)-6-hexylnaphthalene-   2-(3-Fluorophenyl)-6-heptylnaphthalene-   2-(3-Fluorophenyl)-6-(3-butenyl)naphthalene-   2-(3,5-Difluorophenyl)-6-ethylnaphthalene-   2-(3,5-Difluorophenyl)-6-propylnaphthalene-   2-(3,5-Difluorophenyl)-6-butylnaphthalene-   2-(3,5-Difluorophenyl)-6-pentylnaphthalene-   2-(3,5-Difluorophenyl)-6-hexylnaphthalene-   2-(3,5-Difluorophenyl)-6-heptylnaphthalene-   2-(3,5-Difluorophenyl)-6-(3-butenyl)naphthalene-   2-Phenyl-6-ethylnaphthalene-   2-Phenyl-6-propylnaphthalene-   2-Phenyl-6-butylnaphthalene-   2-Phenyl-6-pentylnaphthalene-   2-Phenyl-6-hexylnaphthalene-   2-Phenyl-6-heptylnaphthalene-   2-Phenyl-6-(3-butenyl)naphthalene-   2-(4-Chlorophenyl)-6-ethylnaphthalene-   2-(4-Chlorophenyl)-6-propylnaphthalene-   2-(4-Chlorophenyl)-6-butylnaphthalene-   2-(4-Chlorophenyl)-6-pentylnaphthalene-   2-(4-Chlorophenyl)-6-hexylnaphthalene-   2-(4-Chlorophenyl)-6-heptylnaphthalene-   2-(4-Chlorophenyl)-6-(3-butenyl)naphthalene-   2-(3-Fluoro-4-chlorophenyl)-6-ethylnaphthalene-   2-(3-Fluoro-4-chlorophenyl)-6-propylnaphthalene-   2-(3-Fluoro-4-chlorophenyl)-6-butylnaphthalene-   2-(3-Fluoro-4-chlorophenyl)-6-pentylnaphthalene-   2-(3-Fluoro-4-chlorophenyl)-6-hexylnaphthalene-   2-(3-Fluoro-4-chlorophenyl)-6-heptylnaphthalene-   2-(3-Fluoro-4-chlorophenyl)-6-(3-butenyl)naphthalene-   2-(3,5-Difluoro-4-chlorophenyl)-6-ethylnaphthalene-   2-(3,5-Difluoro-4-chlorophenyl)-6-propylnaphthalene-   2-(3,5-Difluoro-4-chlorophenyl)-6-butylnaphthalene-   2-(3,5-Difluoro-4-chlorophenyl)-6-pentylnaphthalene-   2-(3,5-Difluoro-4-chlorophenyl)-6-hexylnaphthalene-   2-(3,5-Difluoro-4-chlorophenyl)-6-heptylnaphthalene-   2-(3,5-Difluoro-4-chlorophenyl)-6-(3-butenyl)naphthalene-   2-(4-Trifluoromethoxyphenyl)-6-ethylnaphthalene-   2-(4-Trifluoromethoxyphenyl)-6-propylnaphthalene-   2-(4-Trifluoromethoxyphenyl)-6-butylnaphthalene-   2-(4-Trifluoromethoxyphenyl)-6-pentylnaphthalene-   2-(4-Trifluoromethoxyphenyl)-6-hexylnaphthalene-   2-(4-Trifluoromethoxyphenyl)-6-heptylnaphthalene-   2-(4-Trifluoromethoxyphenyl)-6-(3-butenyl)naphthalene-   2-(3-Fluoro-4-trifluoromethoxyphenyl)-6-ethylnaphthalene-   2-(3-Fluoro-4-trifluoromethoxyphenyl)-6-propylnaphthalene-   2-(3-Fluoro-4-trifluoromethoxyphenyl)-6-butylnaphthalene-   2-(3-Fluoro-4-trifluoromethoxyphenyl)-6-pentylnaphthalene-   2-(3-Fluoro-4-trifluoromethoxyphenyl)-6-hexylnaphthalene-   2-(3-Fluoro-4-trifluoromethoxyphenyl)-6-heptylnaphthalene-   2-(3-Fluoro-4-trifluoromethoxyphenyl)-6-(3-butenyl)naphthalene-   2-(3,5-Difluoro-4-trifluoromethoxyphenyl)-6-ethylnaphthalene-   2-(3,5-Difluoro-4-trifluoromethoxyphenyl)-6-propylnaphthalene-   2-(3,5-Difluoro-4-trifluoromethoxyphenyl)-6-butylnaphthalene-   2-(3,5-Difluoro-4-trifluoromethoxyphenyl)-6-pentylnaphthalene-   2-(3,5-Difluoro-4-trifluoromethoxyphenyl)-6-hexylnaphthalene-   2-(3,5-Difluoro-4-trifluoromethoxyphenyl)-6-heptylnaphthalene-   2-(3,5-Difluoro-4-trifluoromethoxyphenyl)-6-(3-butenyl)naphthalene-   2-(4-Difluoromethoxyphenyl)-6-ethylnaphthalene-   2-(4-Difluoromethoxyphenyl)-6-propylnaphthalene-   2-(4-Difluoromethoxyphenyl)-6-butylnaphthalene-   2-(4-Difluoromethoxyphenyl)-6-pentylnaphthalene-   2-(4-Difluoromethoxyphenyl)-6-hexylnaphthalene-   2-(4-Difluoromethoxyphenyl)-6-heptylnaphthalene-   2-(4-Difluoromethoxyphenyl)-6-(3-butenyl)naphthalene-   2-(3-Fluoro-4-difluoromethoxyphenyl)-6-ethylnaphthalene-   2-(3-Fluoro-4-difluoromethoxyphenyl)-6-propylnaphthalene-   2-(3-Fluoro-4-difluoromethoxyphenyl)-6-butylnaphthalene-   2-(3-Fluoro-4-difluoromethoxyphenyl)-6-pentylnaphthalene-   2-(3-Fluoro-4-difluoromethoxyphenyl)-6-hexylnaphthalene-   2-(3-Fluoro-4-difluoromethoxyphenyl)-6-heptylnaphthalene-   2-(3-Fluoro-4-difluoromethoxyphenyl)-6-(3-butenyl)naphthalene-   2-(3,5-Difluoro-4-difluoromethoxyphenyl)-6-ethylnaphthalene-   2-(3,5-Difluoro-4-difluoromethoxyphenyl)-6-propylnaphthalene-   2-(3,5-Difluoro-4-difluoromethoxyphenyl)-6-butylnaphthalene-   2-(3,5-Difluoro-4-difluoromethoxyphenyl)-6-pentylnaphthalene-   2-(3,5-Difluoro-4-difluoromethoxyphenyl)-6-hexylnaphthalene-   2-(3,5-Difluoro-4-difluoromethoxyphenyl)-6-heptylnaphthalene-   2-(3,5-Difluoro-4-difluoromethoxyphenyl)-6-(3-butenyl)naphthalene-   2-[4-(3,4-Difluorophenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3,4-Difluorophenyl)phenyl]-6-propylnaphthalene-   2-[4-(3,4-Difluorophenyl)phenyl]-6-butylnaphthalene-   2-[4-(3,4-Difluorophenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3,4-Difluorophenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3,4-Difluorophenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3,4-Difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3,4,5-Trifluorophenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3,4,5-Trifluorophenyl)phenyl]-6-propylnaphthalene-   2-[4-(3,4,5-Trifluorophenyl)phenyl]-6-butylnaphthalene-   2-[4-(3,4,5-Trifluorophenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3,4,5-Trifluorophenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3,4,5-Trifluorophenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3,4,5-Trifluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(4-Fluorophenyl)phenyl]-6-ethylnaphthalene-   2-[4-(4-Fluorophenyl)phenyl]-6-propylnaphthalene-   2-[4-(4-Fluorophenyl)phenyl]-6-butylnaphthalene-   2-[4-(4-Fluorophenyl)phenyl]-6-pentylnaphthalene-   2-[4-(4-Fluorophenyl)phenyl]-6-hexylnaphthalene-   2-[4-(4-Fluorophenyl)phenyl]-6-heptylnaphthalene-   2-[4-(4-Fluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3-Fluorophenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3-Fluorophenyl)phenyl]-6-propylnaphthalene-   2-[4-(3-Fluorophenyl)phenyl]-6-butylnaphthalene-   2-[4-(3-Fluorophenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3-Fluorophenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3-Fluorophenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3-Fluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-propylnaphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-butylnaphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-propylnaphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-butylnaphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3,5-Difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(4-Chlorophenyl)phenyl]-6-ethylnaphthalene-   2-[4-(4-Chlorophenyl)phenyl]-6-propylnaphthalene-   2-[4-(4-Chlorophenyl)phenyl]-6-butylnaphthalene-   2-[4-(4-Chlorophenyl)phenyl]-6-pentylnaphthalene-   2-[4-(4-Chlorophenyl)phenyl]-6-hexylnaphthalene-   2-[4-(4-Chlorophenyl)phenyl]-6-heptylnaphthalene-   2-[4-(4-Chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene-   2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene-   2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3-Fluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3,5-Difluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3,5-Difluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene-   2-[4-(3,5-Difluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene-   2-[4-(3,5-Difluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3,5-Difluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3,5-Difluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3,5-Difluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(4-Trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(4-Trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[4-(4-Trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[4-(4-Trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(4-Trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(4-Trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(4-Trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[4-(3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[4-(3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3-Fluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(4-Difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(4-Difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[4-(4-Difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[4-(4-Difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(4-Difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(4-Difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(4-Difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3-Fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3-Fluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[4-(3-Fluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[4-(3-Fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3-Fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3-Fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3-Fluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3,5-Difluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(4-Trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(4-Trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   2-[4-(4-Trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   2-[4-(4-Trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(4-Trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(4-Trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(4-Trifluoromethylphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3-Fluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3-Fluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   2-[4-(3-Fluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   2-[4-(3-Fluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3-Fluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3-Fluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3-Fluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3,5-Difluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(4-Methoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(4-Methoxyphenyl)phenyl]-6-propylnaphthalene-   2-[4-(4-Methoxyphenyl)phenyl]-6-butylnaphthalene-   2-[4-(4-Methoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(4-Methoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(4-Methoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(4-Methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3-Fluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3-Fluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene-   2-[4-(3-Fluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene-   2-[4-(3-Fluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3-Fluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3-Fluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3-Fluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene-   2-[4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene-   2-[4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(3,5-Difluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(4-Allyloxyphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(4-Allyloxyphenyl)phenyl]-6-propylnaphthalene-   2-[4-(4-Allyloxyphenyl)phenyl]-6-butylnaphthalene-   2-[4-(4-Allyloxyphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(4-Allyloxyphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(4-Allyloxyphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(4-Allyloxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-(4-Methylphenyl)phenyl]-6-ethylnaphthalene-   2-[4-(4-Methylphenyl)phenyl]-6-propylnaphthalene-   2-[4-(4-Methylphenyl)phenyl]-6-butylnaphthalene-   2-[4-(4-Methylphenyl)phenyl]-6-pentylnaphthalene-   2-[4-(4-Methylphenyl)phenyl]-6-hexylnaphthalene-   2-[4-(4-Methylphenyl)phenyl]-6-heptylnaphthalene-   2-[4-(4-Methylphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-ethylnaphthalene-   2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-propylnaphthalene-   2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-butylnaphthalene-   2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-pentylnaphthalene-   2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-hexylnaphthalene-   2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-heptylnaphthalene-   2-[4-[4-(3-Butenyl)phenyl]phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3,4-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(4-fluorophenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(4-fluorophenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(4-fluorophenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(4-fluorophenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(4-fluorophenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(4-fluorophenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(4-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3-fluorophenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3-fluorophenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3-fluorophenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3-fluorophenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3-fluorophenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3-fluorophenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3-fluorophenyl) phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3,5-Difluorophenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(4-trifluoromethylphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3fluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(4-allyloxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-(4-methylphenyl)phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-(4-methylphenyl)phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-(4-methylphenyl)phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-(4-methylphenyl)phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-(4-methylphenyl)phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-(4-methylphenyl)phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-(4-methylphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-ethylnaphthalene-   2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-propylnaphthalene-   2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-butylnaphthalene-   2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-pentylnaphthalene-   2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-hexylnaphthalene-   2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-heptylnaphthalene-   2-[3-Fluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3,4-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3,4,5-trifluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(4-fluorophenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(4-fluorophenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(4-fluorophenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(4-fluorophenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(4-fluorophenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(4-fluorophenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(4-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3-fluorophenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3-fluorophenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3-fluorophenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3-fluorophenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3-fluorophenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3-fluorophenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3-fluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(4-chlorophenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(4-chlorophenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(4-chlorophenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(4-chlorophenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(4-chlorophenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(4-chlorophenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3,5difluoro-4-chlorophenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-chlorophenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(4-trifluoromethylphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-trifluoromethylphenylphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(4-methoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(4-methoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3-fluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(3,5-difluoro-4-methoxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(4-allyloxyphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-(4-methylphenyl)phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-(4-methylphenyl)phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-(4-methylphenyl)phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-(4-methylphenyl)phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-(4-methylphenyl)phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-(4-methylphenyl)phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-(4-methylphenyl)phenyl]-6-(3-butenyl)naphthalene-   2-[3,5-Difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-ethylnaphthalene-   2-[3,5-Difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-propylnaphthalene-   2-[3,5-Difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-butylnaphthalene-   2-[3,5-Difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-pentylnaphthalene-   2-[3,5-Difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-hexylnaphthalene-   2-[3,5-Difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-heptylnaphthalene-   2-[3,5-Difluoro-4-[4-(3-butenyl)phenyl]phenyl]-6-(3-butenyl)naphthalene

Example 14 Synthesis of 6-fluoro-2-(trans-4-propylcyclohexyl)naphthalene

3.38 g of 6-fluoro-2-bromonaphthalene (synthesized by converting6-bromo-2-naphthylamine to a diazonium salt of tetrafluoroboric acid,and then subjecting the diazonium salt to thermal decomposition) wasdissolved in 30 ml of tetrahydrofuran (THF), and then cooled to atemperature of −40° C. under a nitrogen atmosphere. To the reactionsolution was then added dropwise 10 ml of n-butyl lithium (1.5 M hexanesolution) in 5 minutes. The reaction mixture was then further stirred.The reaction solution was then returned to room temperature. To thereaction solution was then added dropwise a solution of 2.20 g of4-propylcyclohexanene in 10 ml of THF in 5 minutes. The reaction mixturewas then stirred for 1 hour. To the reaction solution were then addedwater and a small amount of diluted hydrochloric acid. The reactionsolution was extracted with 50 ml of toluene, washed with water and thenwith saturated brine, and then dehydrated and dried over anhydroussodium sulfate. To the residue was then added 300 mg ofp-toluenesulfonic acid monohydrate. The reaction mixture was then heatedunder reflux while the azeotropically distilled water was being drivenout of the system for 2 hours. The reaction solution was allowed tocool, washed sequentially with water, saturated aqueous solution ofsodium bicarbonate, water and saturated brine, and then dehydrated anddried over anhydrous sodium sulfate. The solvent was distilled off toobtain a crude crystal which was then purified through silica gel columnchromatography (hexane) to obtain 2.1 g of6-fluoro-2-(4-propylcyclohexenyl)naphthalene in the form of whitecrystal. The total amount of6-fluoro-2-(4-propylcyclohexenyl)naphthalene was dissolved in 20 ml ofethyl acetate. To the solution was then added 200 mg of 5% palladiumcarbon. The reaction mixture was then stirred at a hydrogen pressure of4 atm for 5 hours. The catalyst was then removed by filtration throughCelite. The solvent was then distilled off to obtain 2.1 g of6-fluoro-2-(4-propylcyclohexyl)naphthalene in the form of crude product(cis/trans mixture). The crude product was then dissolved in 20 ml ofN,N-dimethylformamide (DMF). To the reaction mixture was then added 400mg of potassium t-butoxide. The reaction mixture was then stirred at atemperature of from 40° C. to 50° C. for 1 hour. To the reaction mixturewere then added hexane and water. The reaction mixture was then treatedwith diluted hydrochloric acid to become weakly acidic. The resultinghexane phase was then separated. The resulting aqueous phase was thenextracted with hexane. The material thus extracted and the hexane phasewere together washed with water and saturated brine. The solvent wasthen distilled off. The residue was purified through silica gel columnchromatography (hexane), and then recrystallized twice from ethanol toobtain 0.75 g of 6-fluoro-2-(trans-4-propylcyclohexyl)naphthalene in theform of white crystal.

Example 15 Synthesis of5,6-difluoro-2-(trans-4-pentylcyclohexyl)naphthalene

The procedure of Example 14 was followed except that5,6-difluoro-2-bromonaphthalene (synthesized by converting6-bromo-1-fluoro-2-naphthylamine to a diazonium salt of tetrafluoroboricacid, and then subjecting the diazonium salt to thermal decomposition)was used instead of 6-fluoro-2-bromonaphthalene and4-pentylcyclohexanene was used instead of 4-propylcyclohexanene toobtain 5,6-difluoro-2-(trans-4-pentylcyclohexyl)naphthalene.

The following compounds were prepared in the same manner as mentionedabove.

-   6-Fluoro-2-(trans-4-pentylcyclohexyl)naphthalene-   6-Fluoro-2-(trans-4-heptylcyclohexyl)naphthalene-   6-Fluoro-2-(trans-4-methoxymethylcyclohexyl)naphthalene-   5,6-Difluoro-2-(trans-4-propylcyclohexyl)naphthalene-   5,6-Difluoro-2-(trans-4-heptylcyclohexyl)naphthalene-   5,6,7-Trifluoro-2-(trans-4-propylcyclohexyl)naphthalene-   5,6,7-Trifluoro-2-(trans-4-pentylcyclohexyl)naphthalene-   5,6,7-Trifluoro-2-(trans-4-heptylcyclohexyl)naphthalene-   6-Fluoro-2-(trans-4′-ethylbicyclohexane-trans-4-yl)naphthalene-   6-Fluoro-2-(trans-4′-propylbicyclohexane-trans-4-yl)naphthalene-   6-Fluoro-2-(trans-4′-butylbicyclohexane-trans-4-yl)naphthalene-   6-Fluoro-2-(trans-4′-pentylbicyclohexane-trans-4-yl)naphthalene-   5,6-Difluoro-2-(trans-4′-ethylbicyclohexane-trans-4-yl)naphthalene-   5,6-Difluoro-2-(trans-4′-propylbicyclohexane-trans-4-yl)naphthalene-   5,6-Difluoro-2-(trans-4′-butylbicyclohexane-trans-4-yl)naphthalene-   5,6-Difluoro-2-(trans-4′-pentylbicyclohexane-trans-4-yl)naphthalene-   5,6,7-Trifluoro-2-(trans-4′-ethylbicyclohexane-trans-4-yl)naphthalene-   5,6,7-Trifluoro-2-(trans-4′-propylbicyclohexane-trans-4-yl)naphthalene-   5,6,7-Trifluoro-2-(trans-4′-butylbicyclohexane-trans-4-yl)naphthalene-   5,6,7-Trifluoro-2-(trans-4′-pentylbicyclohexane-trans-4-yl)naphthalene-   4,5,6,7-Tetrafluoro-2-(trans-4′-ethylbicyclohexane-trans-4-yl)naphthalene-   4,5,6,7-Tetrafluoro-2-(trans-4′-propylbicyclohexane-trans-4-yl)naphthalene-   4,5,6,7-Tetrafluoro-2-(trans-4′-butylbicyclohexane-trans-4-yl)naphthalene-   4,5,6,7-Tetrafluoro-2-(trans-4′-pentylbicyclohexane-trans-4-yl)naphthalene-   6-Fluoro-2-[trans-4-[2-(trans-4-ethylcyclohexyl)ethyl]cyclohexyl]naphthalene-   6-Fluoro-2-[trans-4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexyl]naphthalene-   6-Fluoro-2-[trans-4-[2-(trans-4-butylcyclohexyl)ethyl]cyclohexyl]naphthalene-   6-Fluoro-2-[trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexyl]naphthalene-   5,6-Difluoro-2-[trans-4-[2-(trans-4-ethylcyclohexyl)ethyl]cyclohexyl]naphthalene-   5,6-Difluoro-2-[trans-4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexyl]naphthalene-   5,6-Difluoro-2-[trans-4-[2-(trans-4-butylcyclohexyl)ethyl]cyclohexyl]naphthalene-   5,6-Difluoro-2-[trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexyl]naphthalene-   5,6,7-Trifluoro-2-[trans-4-[2-(trans-4-ethylcyclohexyl)ethyl]cyclohexyl]naphthalene-   5,6,7-Trifluoro-2-[trans-4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexyl]naphthalene-   5,6,7-Trifluoro-2-[trans-4-[2-(trans-4-butylcyclohexyl)ethyl]cyclohexyl]naphthalene-   5,6,7-Trifluoro-2-[trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexyl]naphthalene

Example 16 Synthesis of5,6-difluoro-2-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene

The procedure of Example 14 was followed except that5,6-difluoro-2-bromonaphthalene was used instead of6-fluoro-2-bromonaphthalene, 4-propylcyclohexaneethanal was used insteadof 4-propylcyclohexanene and isomerization with potassium t-butoxide wasnot effected to obtain5,6-difluoro-2-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene.

The following compounds were prepared in the same manner as mentionedabove.

-   5,6-Difluoro-2-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   5,6-Difluoro-2-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   6-Fluoro-2-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   6-Fluoro-2-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   6-Fluoro-2-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   5,6,7-Trifluoro-2-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   5,6,7-Trifluoro-2-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   5,6,7-Trifluoro-2-[2-(trans-4-heptylcyclohexyl)ethyl]naphthalene-   6-Fluoro-2-[2-(trans-4′-ethylbicyclohexane-trans-4-yl)ethyl]naphthalene-   6-Fluoro-2-[2-(trans-4′-propylbicyclohexane-trans-4-yl)    ethyl]naphthalene-   6-Fluoro-2-[2-(trans-4′-butylbicyclohexane-trans-4-yl)ethyl]naphthalene-   6-Fluoro-2-[2-(trans-4′-pentylbicyclohexane-trans-4-yl)ethyl]naphthalene-   5,6-Difluoro-2-[2-(trans-4′-ethylbicyclohexane-trans-4-yl)ethyl]naphthalene-   5,6-Difluoro-2-[2-(trans-4′-propylbicyclohexane-trans-4-yl)ethyl]naphthalene-   5,6-Difluoro-2-[2-(trans-4′-butylbicyclohexane-trans-4-yl)ethyl]naphthalene-   5,6-Difluoro-2-[2-(trans-4′-pentylbicyclohexane-trans-4-yl)ethyl]naphthalene-   5,6,7-Trifluoro-2-[2-(trans-4′-ethylbicyclohexane-trans-4-yl)ethyl]naphthalene-   5,6,7-Trifluoro-2-[2-(trans-4′-propylbicyclohexane-trans-4-yl)ethyl]naphthalene(1–5)    5,6,7-Trifluoro-2-[2-(trans-4′-butylbicyclohexane-trans-4-yl)ethyl]naphthalene-   5,6,7-Trifluoro-2-[2-(trans-4′-pentylbicyclohexane-trans-4-yl)ethyl]naphthalene-   6-Fluoro-2-[2-[4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene-   6-Fluoro-2-[2-[4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene-   5,6-Difluoro-2-[2-[4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene-   5,6-Difluoro-2-[2-[4-(trans-4-pentylcyclohexyl)    phenyl]ethyl]naphthalene-   5,6,7-Trifluoro-2-[2-[4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene-   5,6,7-Trifluoro-2-[2-[4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene-   6-Fluoro-2-[2-[2–6-difluoro-4-(trans-4-propyloyclohexyl)    phenyl]ethyl]naphthalene-   6-Fluoro-2-[2-[2–6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene-   5,6-Difluoro-2-[2-[2–6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene-   5,6-Difluoro-2-[2-[2–6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene-   5,6,7-Trifluoro-2-[2-[2–6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene-   5,6,7-Trifluoro-2-[2-[2–6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene

Example 17 Synthesis of5,6-difluoro-2-(trans-4′-vinylbicyclohexane-trans-4-yl)naphthalene

The procedure of Example 14 was followed except that5,6-difluoro-2-bromonaphthalene was used instead of6-fluoro-2-bromonaphthalene andbicyclohexane-4,4′-dionemonoethyleneacetal was used instead of4-propylcyclohexanene. The foregoing procedure wan followed bydeacetalation with formic acid to obtaintrans-4′-(5,6-difluoronaphthyl)bicyclohexane-4-one. Separately, a Wittigreagent was prepared from methoxymethyltriphenylphosphonium chloride andpotassium t-butoxide in THF under cooling with ice. To the Wittigreagent was then added dropwise a solution of the foregoingtrans-4′-(5,6-difluoronaphthyl)bicyclohexane-4-one at a temperature of0° C. After 1 hour of reaction, the reaction solution was then returnedto room temperature. To the reaction solution was then added water. Theresulting organic phase was then concentrated. To the organic phase wasthen added hexane to make a solution. Insoluble triphenylphosphine oxidewas then removed by filtration. The residue was then washed with a 1/1mixture of methanol and water. The resulting hexane phase was thenconcentrated to obtain a crude product. The crude product was thendissolved in ethanol. To the solution was then added an ethanol solutionof potassium hydroxide. The reaction mixture was then stirred at roomtemperature for 1 hour. To the reaction solution was then added water.The reaction solution was neutralized with diluted hydrochloric acid,and then neutralized with toluene. The resulting organic phase waswashed with water, and then dehydrated and dried over anhydrous sodiumsulfate. The solvent was then distilled off to obtaintrans-4′-(5,6-difluoronaphthyl)bicyclohexane-trans-4-carbaldehyde incrystal form. The crystal was then reacted with a Wittig reagentprepared from methoxymethyltriphenylphosphonium iodide and potassiumt-butoxide to obtain5,6-difluoro-2-(trans-4′-vinylbicyclohexane-trans-4-yl)naphthalene.

The following compounds were prepared in the same manner as mentionedabove.

-   5,6-Difluoro-2-[trans-4′-(3-butenyl)bicyclohexane-trans-4-yl]naphthalene-   6-Fluoro-2-(trans-4′-vinylbicyclohexane-trans-4-yl)naphthalene-   6-Fluoro-2-[trans-4′-(3-butenyl)bicyclohexane-trans-4-yl]naphthalene-   5,6,7-Trifluoro-2-(trans-4-vinylbicyclohexane-trans-4-yl)naphthalene-   5,6,7-Trifluoro-2-[trans-4′-(3-butenyl)bicyclohexane-trans-4-yl]naphthalene-   4,5,6,7-Tetrafluoro-2-(trans-4′-vinylbicyclohexane-trans-4-yl)naphthalene-   4,5,6,7-Tetrafluoro-2-[trans-4′-(3-butenyl)    bicyclohexane-trans-4-yl]naphthalene-   6-Fluoro-2-(trans-4-vinylcyclohexyl)naphthalene-   6-Fluoro-2-[trans-4(3-butenyl)cyclohexyl]naphthalene-   5,6-Difluoro-2-(trans-4-vinylcyclohexyl)naphthalene-   5,6-Difluoro-2-[trans-4-(3-butenyl)cyclohexyl]naphthalene-   5,6,7-Trifluoro-2-(trans-4-vinylcyclohexyl)naphthalene-   5,6,7-Trifluoro-2-[trans-4-(3-butenyl)cyclohexyl]naphthalene

Example 18 Synthesis of5,6-difluoro-2-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene

To a THF solution of an organic lithium reagent prepared from5,6-difluoro-2-bromonaphthalene were added dropwise4-iodo-1-(trans-4-propylcyclohexyl)benzene and a THF solution oftetrakis(triphenylphosphine)palladium (0) in the catalytic amount. Thereaction mixture was then stirred at room temperature for 3 hours. Tothe reaction mixture were then added water and toluene to terminate thereaction. To the reaction solution was then added diluted hydrochloricacid until the aqueous phase became weakly acidic. The reaction solutionwas then extracted with toluene. The material thus extracted and theorganic phase were together washed with water and then with saturatedbrine, and then dried over anhydrous sodium sulfate. The solvent wasdistilled off under reduced pressure to obtain an oily matter. The oilymatter was purified through silica gel column chromatography (hexane),and then recrystallized from ethanol to obtain5,6-difluoro-2-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene in theform of white crystal.

The following compounds were prepared in the same manner as mentionedabove.

-   5,6-Difluoro-2-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   5,6-Difluoro-2-[4-(trans-4-butylcyclohexyl)phenyl)naphthalene-   5,6-Difluoro-2-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   5,6-Difluoro-2-[4-(trans-4-vinylcyclohexyl)phenyl]naphthalene-   6-Fluoro-2-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   6-Fluoro-2-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   6-Fluoro-2-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   6-Fluoro-2-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   6-Fluoro-2-[4-(trans-4-vinylcyclohexyl)phenyl]naphthalene-   5,6,7-Trifluoro-2-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   5,6,7-Trifluoro-2-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   5,6,7-Trifluoro-2-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   5,6,7-Trifluoro-2-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   5,6,7-Trifluoro-2-[4-(trans-4-vinylcyclohexyl)phenyl]naphthalene-   4,5,6,7-Tetrafluoro-2-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   4,5,6,7-Tetrafluoro-2-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   4,5,6,7-Tetrafluoro-2-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   4,5,6,7-Tetrafluoro-2-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   4,5,6,7-Tetrafluoro-2-[4-(trans-4-vinylcyclohexyl)phenyl]naphthalene-   6-Fluoro-2-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   6-Fluoro-2-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   6-Fluoro-2-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   6-Fluoro-2-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   6-Fluoro-2-[2,6-difluoro-4-(trans-4-vinylcyclohexyl)phenyl]naphthalene-   5,6-Difluoro-2-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   5,6-Difluoro-2-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   5,6-Difluoro-2-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   5,6-Difluoro-2-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   5,6-Difluoro-2-[2,6-difluoro-4-(trans-4-vinylcyclohexyl)phenyl]naphthalene-   5,6,7-Trifluoro-2-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   5,6,7-Trifluoro-2-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   5,6,7-Trifluoro-2-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   5,6,7-Trifluoro-2-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   5,6,7-Trifluoro-2-[2,6-difluoro-4-(trans-4-vinylcyclohexyl)phenyl]naphthalene-   4,5,6,7-Tetrafluoro-2-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   4,5,6,7-Tetrafluoro-2-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   4,5,6,7-Tetrafluoro-2-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   4,5,6,7-Tetrafluoro-2-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   4,5,6,7-Tetrafluoro-2-[2,6-difluoro-4-(trans-4-vinylcyclohexyl)phenyl]naphthalene-   5,6-Difluoro-2-(2-fluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   5,6-Difluoro-2-[2-fluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   5,6-Difluoro-2-[2-fluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   5,6-Difluoro-2-[2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene

Example 19 Synthesis of1-fluoro-2-trifluoromethoxy-6-(trans-4-propylcyclohexyl)naphthalene

1.5 g of sodium hydride was suspended in 5 ml of tetrahydrofuran (THF)under cooling by an ice-water bath. To the suspension was then addeddropwise 40 ml THF solution of 10.0 g of1-fluoro-6-(trans-4-propylcyclohexyl)naphthalene-2-ol (obtained byreacting a Grignard reagent prepared from 6-bromo-2-methoxynaphthaleneand magnesium with 4-propylcyclohexanene, subjecting the product todehydration in the presence of an acid to obtain a naphthylcyclohexenederivative, subjecting the naphthylcyclohexene derivative to catalyticreduction, treating the material with a strongly basic potassiumt-butoxide in DMF so that the cyclohexane ring was isomerized to transform, subjecting the material to demethylation with hydrobromic acid,and then fluorinating the material withN-fluoro-5-trifluoromethoxypyridinium-2-sulfonate). After several hoursof stirring, to the reaction solution was then added dropwise 30 ml of aTHF solution of 7.4 g of S-ethyl chlorodithiocarbonate. After 1 hour ofstirring, to the reaction solution was than added 20 ml of water toterminate the reaction. To the reaction solution was then added 50 ml ofethyl acetate. The organic phase was further washed twice with 20 ml ofwater, and then dehydrated and dried over anhydrous sodium sulfate.Subsequently, the solvent was distilled off under reduced pressure toobtain 12.0 g ofS-ethyl-O-1-fluoro-6-(trans-4-propylcyclohexyl)naphthalene-2-yldithiocarbonate. 12.0 g ofS-ethyl-O-1-fluoro-6-(trans-4-propylcyclohexyl)naphthalene-2-yldithiocarbonate thus obtained was dissolved in 48 ml of dichloromethane,and then added dropwise to 1 liter dichloromethane solution of 300 g ofhydrogen fluoride-melamine complex and 1,3-dibromo-5,5-dimethylhydantoinwhich had been cooled to a temperature of 0° C. After 30 minutes ofstirring, to the reaction solution was then added 200 ml of water toterminate the reaction. The resulting organic phase was washed twicewith 200 ml of water, and then dehydrated and dried over anhydroussodium sulfate. The solvent was then distilled off. The residue was thenpurified through silica gel column chromatography (developing solvent:hexane). The total amount of the purified product was then dissolved in50 ml of THF. Two the solution was then added dropwise 43 ml of a 1.6 Mhexane solution of butyl lithium at a temperature of −78° C. After thetermination of dropwise addition, the reaction mixture was then stirredfor 10 minutes. To the reaction mixture was then added 10 ml of water.The reaction mixture was then returned to room temperature. To thereaction mixture was then added 20 ml of water. The resulting organicphase was washed twice with 20 ml of water, and then dehydrated anddried over anhydrous sodium sulfate. The product was purified throughsilica gel column chromatography (hexane/ethyl acetate=9/1), and thenrecrystallized from ethanol to obtain 7.1 g of5-fluoro-5-trifluoromethoxy-2-(trans-4-propylcyclohexyl)naphthalene.

Example 20 Synthesis of1,3-difluoro-2-trifluoromethoxy-6-(trans-4-propylcyclohexyl)naphthalene

The procedure of Example 19 was followed except that1,3-difluoro-6-(trans-4-propylcyclohexyl)naphthalene-2-ol (obtained byreacting a Grignard reagent prepared from1,3-difluoro-6-bromo-2-methoxynaphthalene with 4-propyl cyclohexanene,subjecting the product to dehydration in the presence of an acid toobtain a naphthylcyclohexene derivative, subjecting thenaphthylcyclohexene derivative to catalytic reduction, treating thematerial with a strongly basic potassium t-butoxide in DMF so that thecyclohexane ring was isomerized to trans form, and then subjecting thematerial to demethylation with hydrobromic acid) was used instead of1-fluoro-6-(trans-4-propylcyclohexyl)naphthalene-2-ol to produceS-ethyl-O-1,3-difluoro-6-(trans-4-propylcyclohexyl)naphthalene-2-yldithiocarbonate. The product was then similarly trifluoromethoxylated toobtain5,7-difluoro-6-trifluoromethoxy-2-(trans-4-propylcyclohexyl)naphthalene.

The following compounds were prepared in the same manner as in Example19 or 20.

-   2-Trifluoromethoxy-6-(trans-4-propylcyclohexyl)naphthalene-   2-Trifluoromethoxy-6-(trans-4-butylcyclohexy)naphthalene-   2-Trifluoromethoxy-6-(trans-4-pentylcyclohexyl)naphthalene-   1-Fluoro-2-trifluoromethoxy-6-(trans-4-butylcyclohexyl)naphthalene-   1-Fluoro-2-trifluoromethoxy-6-(trans-4-pentylcyclohexyl)naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(trans-4-butylcyclohexyl)naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(trans-4-pentylcyclohexyl)naphthalene-   trans-4′-Ethyl-trans-4-(2-trifluoromethoxynaphthalene-2-yl)bicyclohexane-   trans-4′-Propyl-trans-4-(2-trifluoromethoxynaphthalene-2-yl)bicyclohexane-   trans-4′-Pentyl-trans-4-(2-trifluoromethoxynaphthalene-2-yl)bicyclohexane-   trans-4′-Ethyl-trans-4-(1-Fluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane-   trans-4′-Propyl-trans-4-(1-Fluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane-   trans-4′-Pentyl-trans-4-(1-Fluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane-   trans-4′-Ethyl-trans-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane-   trans-4′-Propyl-trans-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane-   trans-4′-Pentyl-trans-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane-   trans-4′-Ethyl-trans-4-(1,3,8-trifluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane-   trans-4′-Propyl-trans-4-(1,3,8-trifluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane-   trans-4′-Pentyl-trans-4-(1,3,8-trifluoro-2-trifluoromethoxynaphthalene-2-yl)bicyclohexane-   2-Trifluoromethoxy-6-[4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexyl]naphthalene-   2-Trifluoromethoxy-6-[4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-propylcyclohexyl)ethyl]cyclohexyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexyl]naphthalene

Example 21 Synthesis of1-fluoro-2-trifluoromethoxy-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene

The procedure of Example 20 was followed except that1-fluoro-6-bromo-2-methoxynapthalene was used instead of1,3-difluoro-6-bromo-2-methoxynaphthalene, 4-propylcyclohexane ethanalwas used instead of 4-propylcyclohexanene and isomerization withpotassium t-butoxide was not effected to obtain1-fluoro-2-trifluoromethoxy-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene.

The following compounds were prepared in the same manner as mentionedabove.

-   2-Trifluoromethoxy-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   2-Trifluoromethoxy-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2-(trans-4-propylcyclohexyl)ethyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2-(trans-4-pentylcyclohexyl)ethyl]naphthalene-   Trans-4′-propyl-trans-4-[2-(2-trifluoromethoxynaphthalene-6-yl)ethyl]bicyclohexane-   Trans-4′-pentyl-trans-4-[2-(2-trifluoromethoxynaphthalene-6-yl)ethyl]bicyclohexane-   Trans-4′-propyl-trans-4-[2-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)ethyl]bicyclohexane-   Trans-4′-pentyl-trans-4-[2-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)ethyl]bicyclohexane-   Trans-4′-propyl-trans-4-[2-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)ethyl]bicyclohexane-   Trans-4′-pentyl-trans-4-[2-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)ethyl]bicyclohexane-   2-Trifluoromethoxy-6-[2-[4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene-   2-Trifluoromethoxy-6-[2-[4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-[4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-[4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene-   2-Trifluoromethoxy-6-[2-[3,5-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene-   2-Trifluoromethoxy-6-[2-[3,5-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-[3,5-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-[3,5-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethyl]naphthalene

Example 22 Synthesis of1-fluoro-2-trifluoromethoxy-6-(trans-4′-vinylbicyclohexane-trans-4-yl)naphthalene

A Wittig reagent was prepared from methoxymethyl triphenyl phosphoniumchloride and potassium t-butoxide in THF under cooling with ice. To theWittig reagent was then added a THF solution oftrans-4′-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)bicyclohexane-4-one(obtained by reacting a Grignard reagent prepared from1-fluoro-6-bromo-2-trifluoromethoxynaphthalene withbicyclohexanone-4,4′-dionemonoethyleneacetal, subjecting the product todehydration in the same manner as mentioned above, subjecting theproduct to catalytic reduction, and then deacetalating the product withformic acid) at a temperature of 0° C. After 1 hour of reaction, thereaction solution was returned to room temperature. The reactionsolution was then added water. The resulting organic phase was thenconcentrated. To the material thus concentrated was then added hexane tomake a solution. Insoluble triphenylphosphine oxide was then removed byfiltration. The filtrate was then washed with a 1/1 mixture of methanoland water. The resulting hexane phase was concentrated to obtain a crudeproduct which was then dissolved in ethanol. To the solution was thenadded an ethanol solution of potassium hydroxide. The reaction mixturewas then stirred at room temperature for 1 hour. To the reactionsolution was then added water. The reaction solution was neutralizedwith diluted hydrochloric acid, and then extracted with toluene. Theresulting organic phase was washed with water, and then dehydrated anddried over anhydrous sodium sulfate. The solvent was then distilled offto obtaintrans-4′-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)bicyclohexane-trans-4-carbaldehydein crystal form. The crystal thus obtained was then reacted with aWittig prepared from methoxymethyl triphenyl phosphonium iodide andpotassium t-butoxide to obtain1-fluoro-2-trifluoromethoxy-6-(trans-4′-vinylbicyclohexane-trans-4-yl)naphthalene.

The following compounds were prepared in the same manner as mentionedabove.

-   2-Trifluoromethoxy-6-(trans-4′-vinylbicyclohexane-trans-4-yl)naphthalene-   2-Trifluoromethoxy-6-[trans-4′-(3-butenyl)bicyclohexane6-trans-4-yl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[trans-4′-(3-butenyl)bicyclohexane-trans-4-yl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(trans-4′-vinylbicyclohexane-trans-4-yl)naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[trans-4′-(3-butenyl)bicyclohexane-trans-4-yl]naphthalene-   1,3,8-Trifluoro-2-trifluoromethoxy-6-(trans-4′-vinylbicyclohexane-trans-4-yl)naphthalene-   1,3,8-Trifluoro-2-trifluoromethoxy-6-[trans-4′-(3-butenyl)bicyclohexane-trans-4-yl]naphthalene-   2-Trifluoromethoxy-6-(trans-4-vinylcyclohexyl)naphthalene-   2-Trifluoromethoxy-6-[trans-4-(3-butenyl)cyclohexyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-(trans-4-vinylcyclohexyl)naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[trans-4-(3-butenyl)cyclohexyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(trans-4-vinylcyclohexyl)naphthalene-   1,3Difluoro-2-trifluoromethoxy-6-[trans-4-(3-butenyl)    cyclohexyl]naphthalene

Example 23 Synthesis of1-fluoro-2-trifluoromethoxy-6-(4-propylphenyl)naphthalene

3.4 g of 4-propylphenylboric acid (obtained by reacting a Grignardreagent prepared from 1-bromo-4-propylbenzene with trimethyl borate, andthen subjecting the product to hydrolysis with hydrochloric acid) and25.5 g of 6-bromo-2-naphthol were dissolved in a mixture of 92 ml oftoluene, 46 ml of ethanol and 92 ml of water. To the solution were thenadded 25.5 g of potassium carbonate and 1.3 g oftetrakis(triphenylphosphine)palladium (0). The reaction mixture was thenstirred at a temperature of 75° C. for 7 hours. To the reaction solutionwere then added water and toluene. To the reaction solution was thenadded diluted hydrochloric acid until the aqueous phase became weaklyacidic. The reaction solution was then extracted with toluene. Thematerial thus extracted and the organic phase were together washed withwater and then with saturated brine, and then dried over anhydroussodium sulfate. The solvent was then distilled off under reducedpressure to obtain 41.4 g of 6-(4-propylphenyl)naphthalene-2-ol. 12.7 gof 6-(4-propylphenyl)naphthalene-2-ol was then dissolved in 50 ml ofdichloromethane. To the solution was then added 13.1 g ofN-fluoro-5-trifluoromethoxypyridinium-2-sulfonate. The reaction mixturewas then stirred at room temperature for 18hours. The reaction mixturewas post-treated in the same manner as mentioned above to obtain an oilymatter which was then purified through silica gel column chromatography(hexane/ethyl acetate=9/1) to obtain 10 g of1-fluoro-6-(4-propylphenyl)naphthalene-2-ol. The product was convertedto S-ethyl dithiocarbonate which was then trifluoromethoxylated in thesame manner as in Example 1 to obtain 2.3 g of the titled1-fluoro-2-trifluoromethoxy-6-(4-propylphenyl)naphthalene.

Example 24 Synthesis of1,3-difluoro-2-trifluoromethoxy-6-(4-propylphenyl)naphthalene

7.3 g of 4-propylphenylboric acid and 11 g of1,3-difluoro-2-trifluoromethoxynaphthalene-6-yltrifluoromethanesulfonate (obtained by triflating1,3-difluoro-2-trifluoromethoxynaphthalene-6-ol withtrifluoromethanesulfonic anhydride) were dissolved in 50 ml of DMF. Tothe solution was then added 0.4 g oftetrakis(triphenylphosphine)palladium (0). The reaction mixture wasstirred at a temperature of 85° C. for 8 hours. To the reaction solutionwere then added water and toluene. The resulting aqueous phase was thenextracted with toluene. The material thus extracted and the organicphase were together washed with water and then with saturated brine, andthen dried over anhydrous sodium sulfate. The solvent was then distilledoff under reduced pressure to obtain an oily matter. The oily matterthus obtained was purified through silica gel column chromatography(hexane/ethyl acetate=9/1), and then recrystallized from ethanol toobtain 6.3 g of1,3-difluoro-2-trifluoromethoxy-6-(4-propylphenyl)naphthalene in crystalform.

Example 25 Synthesis of1-fluoro-2-trifluoromethoxy-6-(2-fluoro-4-propylphenyl)naphthalene

The procedure of Example 23 was followed except that2-fluoro-4-propylphenylboric acid was used instead of4-propylphenylboric acid to obtain1-fluoro-2-trifluoromethoxy-6-(2-fluoro-4-propylphenyl)naphthalene.

The following compounds were prepared in the same manner as in Example23, 24 or 25.

-   2-Trifluoromethoxy-6-(4-propylphenyl)naphthalene-   2-Trifluoromethoxy-6-(4-pentylphenyl)naphthalene-   2-Trifluoromethoxy-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-trifluoromethoxy-6-(4-pentylphenyl)naphthalene-   1-Fluoro-2-trifluoromethoxy-6-(4-heptylphenyl)naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[4-(3-butenyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(4-pentylphenyl)naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(4-heptylphenyl)naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[4-(3-butenyl)phenyl]naphthalene-   1,3,8-Trifluoro-2-trifluoromethoxy-6-(4-pentylphenyl)naphthalene-   1,3,8-Trifluoro-2-trifluoromethoxy-6-(4-heptylphenyl)naphthalene-   1,3,8-Trifluoro-2-trifluoromethoxy-6-[4-(3-butenyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-(2-fluoro-4-propylphenyl)naphthalene-   2-Trifluoromethoxy-6-(2-fluoro-4-pentylphenyl)naphthalene-   2-Trifluoromethoxy-6-(2-fluoro-4-heptylphenyl)naphthalene-   2-Trifluoromethoxy-6-[2-fluoro-4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-(2-fluoro-4-pentylphenyl)naphthalene-   1-Fluoro-2-trifluoromethoxy-6-(2-fluoro-4-heptylphenyl)naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-(3-butenyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-(2–6-difluoro-4-propylphenyl)naphthalene-   2-Trifluoromethoxy-6-(2-6-difluoro-4-pentylphenyl)naphthalene-   2-Trifluoromethoxy-6-(2-6-difluoro-4-heptylphenyl)naphthalene-   2-Trifluoromethoxy-6-[2-6-difluoro-4-(3-butenyl)phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-(2-6-difluoro-4-propylphenyl)naphthalene-   1-Fluoro-2-trifluoromethoxy-6-(2-6-difluoro-4-pentylphenyl)naphthalene-   1-Fluoro-2-trifluoromethoxy-6-(2-6-difluoro-4-heptylphenyl)naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-6-difluoro-4-(3-butenyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2-fluoro-4-propylphenyl)naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2-fluoro-4-pentylphenyl)naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2-fluoro-4-heptylphenyl)naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-(3-butenyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-propylphenyl)naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-pentylphenyl)naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-heptylphenyl)naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(3-butenyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   1,3,8-Trifluoro-2-trifluoromethoxy-6-[4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   1,3,8-Trifluoro-2-trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   1,3,8-Trifluoro-2-trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   1,3,8-Trifluoro-2-trifluoromethoxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-[2-fluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-[2-fluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-[2-fluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-[2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl)naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-ethylcyclohexyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]naphthalene-   2-Trifluoromethoxy-6-[4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene-   2-Trifluoromethoxy-6-[4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene-   2-Trifluoromethoxy-6-[2-fluoro-4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene-   2-Trifluoromethoxy-6-[2-fluoro-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene-   2-Trifluoromethoxy-6-[2,6-difluoro-4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene-   2-Trifluoromethoxy-6-[2,6-difluoro-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-[2-(trans-4-propylcyclohexyl)ethyl]phenyl]naphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-[2-(trans-4-pentylcyclohexyl)ethyl]phenyl]naphthalene-   4′-Ethyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-Propyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-Butyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-Pentyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-(3-Butenyl)-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-Ethyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-Propyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-Butyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-Pentyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-(3-Butenyl)-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-ethyl-4-(1,3-Difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-propyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-butyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-pentyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   4′-(3-butenyl)-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-ethyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-propyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-butyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-pentyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-(3-butenyl)-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-ethyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-propyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-butyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-pentyl-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-(3-butenyl)-4-(1-Fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-ethyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-propyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-butyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-pentyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   2′-Fluoro-4′-(3-butenyl)-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-ethyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-propyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-butyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-pentyl-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4t-(3-butenyl)-4-(2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-ethyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-propyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-butyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-pentyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-(3-butenyl)-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-ethyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-propyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-butyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-pentyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3,5-Difluoro-4′-(3-butenyl)-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3-Fluoro-4′-ethyl4-(6-trifluoromethoxynaphthalene-2-yl)biphenyl-   3-Fluoro-4′-propyl4-(6-trifluoromethoxynaphthalene-2-yl)biphenyl-   3-Fluoro-4′-butyl4-(6-trifluoromethoxynaphthalene-2-yl)biphenyl-   3-Fluoro-4′-pentyl4-(6-trifluoromethoxynaphthalene-2-yl)biphenyl-   3-Fluoro-4′-(3-butenyl)-4-(6-trifluoromethoxynaphthalene-2-yl)biphenyl-   3-Fluoro-4′-ethyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3-Fluoro-4′-propyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3-Fluoro-4′-butyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3-Fluoro-4′-pentyl-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3-Fluoro-4′-(3-butenyl)-4-(1-fluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3-Fluoro-4′-ethyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3-Fluoro-4′-propyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3-Fluoro-4′-butyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3-Fluoro-4′-pentyl-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl-   3-Fluoro-4′-(3-butenyl)-4-(1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl)biphenyl

Example 26 Synthesis of1-fluoro-2-trifluoromethoxy-6-1(4-propylphenyl)ethynyl]naphthalene

10 g of 4-propyl-1-ethynylbenzene and 19.5 g of2-bromo-5-fluoro-6-trifluoromethoxynaphthalene were dissolved in 50 mlof N,N-dimethylformamide (DMF). To the solution were then added 50 mg ofcopper iodide (I) and 100 mg of tetrakis(triphenylphosphine)palladium(0). The reaction mixture was then stirred at room temperature for 5hours. To the reaction solution was then added toluene. Insolublematters water removed by filtration. The residue was then washed withwater and saturated brine. The solvent was then distilled off. Theresidue was purified through silica gel column chromatography(hexane/ethyl acetate 9/1), and then recrystallized from ethanol toobtain 8.6 g of1-fluoro-2-trifluoromethoxy-6-[(4-propylphenyl)ethynyl]naphthalene.

The following compounds were prepared in the same manner as mentionedabove.

-   2-Trifluoromethoxy-6-(4-ethylphenyl)ethynylnaphthalene-   2-Trifluoromethoxy-6-(4-propylphenyl)ethynylnaphthalene-   2-Trifluoromethoxy-6-(4-butylphenyl) ethynylnaphthalene-   2-Trifluoromethoxy-6-(4-pentylphenyl) ethynylnaphthalene-   2-Trifluoromethoxy-6-[4-(3-butenyl)phenyl]ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-(4-ethylphenyl)ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-(4-butylphenyl)ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-(4-pentylphenyl)ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-[4-(3-butenyl)phenyl]ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(4-ethylphenyl)ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(4-propylphenyl)ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(4-butylphenyl)ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(4-pentylphenyl)ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[4-(3-butenyl)phenyl]ethynylnaphthalene-   2-Trifluoromethoxy-6-(2-fluoro-4-ethylphenyl)ethynylnaphthalene-   2-Trifluoromethoxy-6-(2-fluoro-4-propylphenyl)ethynylnaphthalene-   2-Trifluoromethoxy-6-(2-fluoro-4-butylphenyl)ethynylnaphthalene-   2-Trifluoromethoxy-6-(2-fluoro-4-pentylphenyl)ethynylnaphthalene-   2-Trifluoromethoxy-6-[2-fluoro-4-(3-butenyl)phenyl]ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-(2-fluoro-4-ethylphenyl)ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-(2-fluoro-4-propylphenyl)ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-(2-fluoro-4-butylphenyl)ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-(2-fluoro-4-pentylphenyl)ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2-fluoro-4-(3-butenyl)phenyl]ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2-fluoro-4-ethylphenyl)ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2-fluoro-4-propylphenyl)ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2-fluoro-4-butylphenyl)ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2-fluoro-4-pentylphenyl)ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2-fluoro-4-(3-butenyl)phenyl]ethynylnaphthalene-   2-Trifluoromethoxy-6-(2,6-difluoro-4-ethylphenyl)ethynylnaphthalene-   2-Trifluoromethoxy-6-(2,6-difluoro-4-propylphenyl)ethynylnaphthalene-   2-Trifluoromethoxy-6-(2,6-difluoro-4-butylphenyl)ethynylnaphthalene-   2-Trifluoromethoxy-6-(2,6-difluoro-4-pentylphenyl)ethynylnaphthalene-   2-Trifluoromethoxy-6-[2,6-difluoro-4-(3-butenyl)phenyl]ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-ethylphenyl)ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-propylphenyl)ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-butylphenyl)ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-pentylphenyl)ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(3-butenyl)phenyl]ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-ethylphenyl)ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-propylphenyl)ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-butylphenyl)ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-(2,6-difluoro-4-pentylphenyl)ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(3-butenyl)phenyl]ethynylnaphthalene-   2-Trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]ethynylnaphthalene-   2-Trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]ethynylnaphthalene-   2-Trifluoromethoxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[4-(trans-4-propylcyclohexyl)phenyl]ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[4-(trans-4-butylcyclohexyl)phenyl]ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[4-(trans-4-pentylcyclohexyl)phenyl]ethynylnaphthalene-   2-Trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethynylnaphthalene-   2-Trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]ethynylnaphthalene-   2-Trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]ethynylnaphthalene-   1-Fluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-propylcyclohexyl)phenyl]ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-butylcyclohexyl)phenyl]ethynylnaphthalene-   1,3-Difluoro-2-trifluoromethoxy-6-[2,6-difluoro-4-(trans-4-pentylcyclohexyl)phenyl]ethynylnaphthalene

Example 27 Synthesis of 2-(4-cyanophenyl)-6-propylnaphthalene

The procedure of Example 9 was followed except that1-fluoro-2-[4-(4,4-dimethyl-1,3-oxazolidine-2-yl)phenyl]-6-propylnaphthalenewas used instead of1-fluoro-2-[4-(4,4-dimethyl-1,3-oxazolidine-2-yl)phenyl]-6-(trans-4-propylcyclohexyl)naphthalene to obtain 2-(4-cyanophenyl)-6-propylnaphthalenein the form of white crystal.

Example 28 Synthesis of 2-(3-fluoro-4-cyanophenyl)-6-propylnaphthalene

The procedure of Example 10 was followed except that1-fluoro-2-(3-fluoro-4-methoxyphenyl)-6-propylnaphthalene was usedinstead of1-fluoro-2-(3-fluoro-4-methoxyphenyl)-6-(trans-4-propylcyclohexyl)naphthaleneto obtain 2-(3-fluoro-4-cyanophenyl)-6-propylnaphthalene in the form ofwhite crystal.

Example 29 Synthesis of2-(3,5-difluoro-4-cyanophenyl)-6-propylnaphthalene

The procedure of Example 11 was followed except that1-fluoro-2-(3,5-difluorophenyl)-6-propylnaphthalene was used instead of1-fluoro-2-(3,5-difluorophenyl)-6-(trans-4-propylcyclohexyl)naphthaleneto obtain 2-(3,5-difluoro-4-cyanophenyl)-6-propylnaphthalene in the formof white crystal.

The following compounds were prepared in the same manner as in Examples27, 28 and 29.

-   1-Fluoro-2-(4-cyanophenyl)-6ethylnaphthalene-   1-Fluoro-2-(4-cyanophenyl)-6-propylnaphthalene-   1-Fluoro-2-(4-cyanophenyl)-6-butylnaphthalene-   1-Fluoro-2-(4-cyanophenyl)-6-pentylnaphthalene-   1-Fluoro-2-(4-cyanophenyl)-6-hexylnaphthalene-   1-Fluoro-2-(4-cyanophenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3-fluoro-4-cyanophenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3-fluoro-4-cyanophenyl)-6-butylnaphthalene-   1-Fluoro-2-(3-fluoro-4-cyanophenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3-fluoro-4-cyanophenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3-fluoro-4-cyanophenyl)-6-heptylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-ethylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-butylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-pentylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-hexylnaphthalene-   1-Fluoro-2-(3,5-difluoro-4-cyanophenyl)-6-heptylnaphthalene-   2-(4-cyanophenyl)-6-ethylnaphthalene-   2-(4-cyanophenyl)-6-propylnaphthalene-   2-(4-cyanophenyl)-6-butylnaphthalene-   2-(4-cyanophenyl)-6-pentylnaphthalene-   2-(4-cyanophenyl)-6-hexylnaphthalene-   2-(4-cyanophenyl)-6-heptylnaphthalene-   2-[3-Fluoro-4-cyanophenyl)-6-ethylnaphthalene-   2-[3-Fluoro-4-cyanophenyl)-6-butylnaphthalene-   2-[3-Fluoro-4-cyanophenyl)-6-pentylnaphthalene-   2-[3-Fluoro-4-cyanophenyl)-6-hexylnaphthalene-   2-[3-Fluoro-4-cyanophenyl)-6-heptylnaphthalene-   2-(3,5-Difluoro-4-cyanophenyl)-6-ethylnaphthalene-   2-(3,5-Difluoro-4-cyanophenyl)-6-butylnaphthalene-   2-(3,5-Difluoro-4-cyanophenyl)-6-pentylnaphthalene-   2-(3,5-Difluoro-4-cyanophenyl)-6-hexylnaphthalene-   2-(3,5-Difluoro-4-cyanophenyl)-6-heptylnaphthalene-   1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3-fluoro-4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3-fluoro-4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3-fluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-ethylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-propylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-butylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-pentylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-hexylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-heptylnaphthalene-   1-Fluoro-2-[3,5-difluoro-4-(3,5-difluoro-4-cyanophenyl)phenyl]-6-(3-butenyl)naphthalene

Example 30 Preparation of Liquid Crystal Composition (1)

A general-purpose host liquid crystal (H) having the followingstructure:

having a wide operating temperature range and a low viscosity which canbe also used for active matrix driving was prepared. The host liquidcrystal composition (H) exhibited a nematic phase at a temperature ofnot higher than 116.7° C. and a melting point of +11° C. The physicalproperties of the liquid crystal composition and the electro-opticalproperties of the liquid crystal device prepared therefrom are asfollows:

Threshold voltage (Vth): 2.14 V Dielectric anisotropy (Δε): 4.8 Response(τr = τd): 25.3 m sec. Birefringence (Δn): 0.090

For the measurement of threshold voltage (Vth) and response, the nematicliquid crystal composition is filled in a TN cell having a thickness of6 μm. The measurement is effected at a temperature of 20° C. The term“response” as used herein is meant to indicate the response time shownduring the application of voltage at which the rise time (τr) and thedrop time (τd) are equal to each other.

80% of the host liquid crystal composition (H) and the compoundrepresented by the formula (Ib-1) of the present invention obtained inExample 15:

were then added to a host liquid crystal composition (H) having a wideoperating temperature range and suitable for low viscosity host liquidcrystal composition, particularly for active matrix driving, in anamount of 20% to prepare a nematic liquid crystal composition (M-1). Asa result, the upper nematic phase temperature limit (T_(N-1)) of thenematic liquid crystal composition (M-1) was 98.2° C. The nematic liquidcrystal composition (M-1) was allowed to stand at a temperature of 150°C. for 20 hours, and then measured for T_(N-1). The results were 97.8°C., demonstrating that the nematic liquid crystal composition (M-1)shows little or no change of T_(N-1) from before heating. The nematicliquid crystal composition (M-1) was then irradiated with ultravioletrays for 20 hours. As a result, the nematic liquid crystal composition(M-1) showed no change of T_(N-1). The nematic liquid crystalcomposition (M-1) was then measured for voltage holding ratio. As aresult, the composition exhibited a sufficiently high voltage holdingratio similarly to the host liquid crystal (H) during preparation, afterheating and after irradiation with ultraviolet rays.

Subsequently, the nematic liquid crystal composition (M-1) was filled ina TN cell having a thickness of 4.5 μm to prepare a liquid crystaldevice. The liquid crystal device was then measured for electro-opticalproperties. The results are as follows:

Upper nematic phase temperature limit (T_(N-1)) 98.6° C. Dielectricanisotropy (Δε) 4.60 Threshold voltage (Vth) 1.76 V Response (τr = τd)24.2 m sec.

It can thus be seen that the addition of the compound (Ib-1) makes itpossible to provide a quick response similarly to the host liquidcrystal composition (H), a lower dielectric anisotropy than the hostliquid crystal composition (H) and a threshold voltage drop of about 10%from that of the host liquid crystal composition (H). The liquid crystaldevice thus obtained was then measured for voltage holding ratio at roomtemperature and 80° C. The results were good at any of the twotemperature ranges, demonstrating that the liquid crystal device can besufficiently used in active matrix driving.

Example 31 Preparation of Liquid Crystal Composition (2)

80% of the host liquid crystal composition (H) and the compound (Ib-2)of the present invention obtained in Example 15:

were added to a host liquid crystal composition (H) having a wideoperating temperature range and suitable for low viscosity host liquidcrystal composition, particularly for active matrix driving, in anamount of 20% to prepare a nematic liquid crystal composition (M-2). Theelectro-optical properties of the nematic liquid crystal composition(M-2) and the liquid crystal device prepared in the same manner asmentioned above therefrom are as follows:

Upper nematic phase temperature limit (T_(N-1)) 92.7° C. Dielectricanisotropy (Δε) 5.7 Threshold voltage (Vth) 1.53 V Response (τr = τd)28.0 m sec.

It can thus be seen that the compound (Ib-1) exhibits a smallerdielectric anisotropy than the host liquid crystal (H) and a thresholdvoltage drop of about 20% from the host liquid crystal (H).

The nematic liquid crystal composition (M-2) was then subjected to heatstability test and ultraviolet ray irradiation test in the same manneras the nematic liquid crystal composition (M-1). As a result, thecomposition (M-2) showed no change of T_(N-1) after these tests. Thenematic liquid crystal composition (M-2) was then measured for voltageholding ratio. As a result, the composition (M-2) exhibited asufficiently high voltage holding ratio during preparation, afterheating and after irradiation with ultraviolet rays.

As mentioned above, the compound represented by the general formula (I)is very useful in the preparation of a liquid crystal composition having(a) a wide nematic phase operating temperature range, (b) a thresholdvoltage low enough to drive at a low voltage, (c) a quick response and(d) a voltage holding ratio high enough active matrix driving.

Example 32 Preparation of Liquid Crystal Composition (2)

80% of the host liquid crystal composition (H) and the compound (Ic-7)of the present invention obtained in Example 2:

were added to a host liquid crystal composition (H) having a wideoperating temperature range and suitable for low viscosity host liquidcrystal composition, particularly for active matrix driving, in anamount of 20% to prepare a nematic liquid crystal composition (M-3). Theelectro-optical properties of the nematic liquid crystal composition(M-3) and the liquid crystal device prepared in the same manner asmentioned above therefrom are as follows:

T_(N-1): 120.0° C. T_(C-N): −2° C. Threshold voltage (Vth) 2.06 VDielectric anisotropy (Δε): 5.5 Birefringence index (Δn): 0.110

It can thus be seen that the addition of the compound (Ic-7) makes itpossible to raise the upper nematic phase temperature limit (T_(N-1)) bynot lower than 3° . The nematic liquid crystal composition (M-3) wascooled to a temperature of −60° C. to undergo crystallization. Thenematic liquid crystal composition (M-3) thus crystallized was thenmeasured for melting point (T_(C-N)) The results were −2° C.,demonstrating that the composition (M-3) exhibits a melting point dropof as much as 13° from the host liquid crystal composition (H).Accordingly, the stable temperature range of nematic phase can beexpanded by as much as about 16°. It can also be seen that the additionof the compound (Ic-7) makes it possible to increase the dielectricanisotropy of liquid crystal composition and lower the threshold voltageof liquid crystal composition. The increase in the birefringence indexcould be suppressed to 0.02 from that of the host liquid crystal (H).

The liquid crystal device was then measured for voltage holding ratio atroom temperature and 80° C. The results were extremely good at any ofthe two temperature ranges, demonstrating that it can be sufficientlyused in active matrix driving.

Comparative Example 1

A compound represented by the following general formula (R-1) having astructure similar to the compound (Ic-7) but having 1,4-phenylene groupinstead of 2,6-naphthylene group:

was added to the host liquid crystal composition (H) in the same amountas mentioned above (20%) to prepare a liquid crystal composition (HR-1).The upper nematic phase temperature limit (T_(N-1)) of the liquidcrystal composition (HR-1) was 101° C., which is far lower than that ofthe composition (M-3) as expected. The liquid crystal composition (HR-1)exhibited a malting point (T_(C-N)) of 5° C., which is higher than thatof the composition (M-3). Accordingly, the liquid crystal composition(HR-1) exhibited a nematic phase temperature range of as much as 25° ormore smaller than the composition (M-3).

Example 33 Preparation of Liquid Crystal Composition (4)

80% of the host liquid crystal composition (H) and the compound (Id-1)of the present invention obtained in Example 12:

were added to a host liquid crystal composition (H) having a wideoperating temperature range and suitable for low viscosity host liquidcrystal composition, particularly for active matrix driving, in anamount of 20% to prepare a nematic liquid crystal composition (M-3). Theelectro-optical properties of the nematic liquid crystal composition(M-3) and the liquid crystal device prepared in the same manner asmentioned above therefrom are as follows:

T_(N-1): 91.0° C. Threshold voltage (Vth) 1.94 V Dielectric anisotropy(Δε): 4.85 Response (τr = τd): 28.4 m sec. Birefringence index (Δn):0.112

It can thus be seen that the addition of the compound (Id-1) in anamount of 20% causes a slight drop of the upper nematic phasetemperature limit (T_(N-1)) but makes it possible to lower the thresholdvoltage of the liquid crystal composition and drastically raise thebirefringence index of the liquid crystal composition (by about 0.02from that of the host liquid crystal composition (H)) withoutdeteriorating the response. Subsequently, the liquid crystal compositionwas allowed to stand at room temperature for 1 month. However, nocrystallization or phase separation were observed. It can thus be seenthat the compound (Id-1) has an excellent miscibility with theconventional liquid crystals. The liquid crystal composition (M-4) wascooled to a temperature of −15° C. to undergo crystallization, and thenmeasured for melting point (T_(C-N)). The results were 14° C.

Example 34 Preparation of Liquid Crystal Composition (5)

To 80% of the host liquid crystal composition (H) was added the compoundrepresented by the formula (Id-2) of the present invention obtained inExample 13:

in the same manner as mentioned above (20%) to prepare a liquid crystalcomposition (M-5). The physical properties of the liquid crystalcomposition (M-5) and the electro-optical properties of the liquidcrystal device prepared in the same manner as mentioned above therefromare as follows:

T_(N-1): 85.1° C. Threshold voltage (Vth) 1.74 V Dielectric anisotropy(Δε): 5.7 Response (τr = τd): 31.1 m sec. Birefringence index (Δn):0.107

The comparison of the liquid crystal composition (M-5) with the liquidcrystal composition (M-4) shows that the liquid crystal composition(M-5) exhibits a slightly lower T_(N-1) and a slightly reducedbirefringence index but has a quick response similarly to the liquidcrystal composition (M-4) and a further drop of threshold voltage.

Example 35 Preparation of Liquid Crystal Composition (6)

To 80% of the host liquid crystal composition (H) was added the compoundrepresented by formula (Id-7) of the present invention obtained inExample 12:

in the same manner am mentioned above (20%) to prepare a liquid crystalComposition (M-6). The physical properties of the liquid crystalcomposition (M-6) and the electro-optical properties of the liquidcrystal device prepared in the same manner as mentioned above therefromare as follows:

T_(N-1): 86.0° C. T_(C-N:) 12° C. Threshold voltage (Vth) 1.65 VDielectric anisotropy (Δε): 6.5 Birefringence index (Δn): 0.107 Response(τr = τd): 28.8 m sec.

The addition of the compound (Id-7) in an amount of 20% causes a slightdrop of the upper nematic phase temperature limit (T_(N-1)) but canprovide a quick response similarly to the host liquid crystalcomposition (H) and makes it possible to drastically lower the thresholdvoltage of the liquid crystal composition (by 0.3 V). Further, thebirefringence index of the liquid crystal composition can be drasticallyincreased from the host liquid crystal composition (H).

Comparative Example 2

The procedure of Examples 33 to 35 were followed except that thecompound represented by formula (Ic) was replaced by a compoundrepresented by the following formula (R-2) having a structure similar tothat of the compound (Ic) but having 1,4-phenylene group instead of2,6-naphthylene group:

which was added in the same manner as mentioned above (20% by weight) toprepare a liquid crystal composition (HR-2). The liquid crystalcomposition (HR-2) thus prepared was then measured for physicalproperties and electro-optical properties in the same manner asmentioned above. The results are as follows:

T_(N-1): 86.0° C. Threshold voltage (Vth) 1.86 V Dielectric anisotropy(Δε): 4.92 Response (τr = τd): 27.0 m sec. Birefringence index (Δn):0.096

The comparison of the liquid crystal composition (HR-2) with the liquidcrystal composition (H-1) shows that the liquid crystal composition(HR-2) exhibits a slightly more quick response and a slightly lowerthreshold voltage (Vth). However, the upper nematic phase temperaturelimit (T_(N-1)) of the liquid crystal composition (HR-2) showed afurther drop. The liquid crystal composition (HR-2) also showed only aslight increase in birefringence index.

The naphthalene derivative provided by the present invention exhibits anexcellent liquid-crystallinity and miscibility with currently widelyused liquid crystal compositions or compositions. The addition of thenaphthalene derivative makes it possible to drastically lower thethreshold voltage of the liquid crystal composition while maintainingits high response. The naphthalene derivative of the present inventionis characterized by a large birefringence index. Further, most of thenaphthalene derivative of the present invention has no strongly polargroup in its molecule and thus can also be used for active matrixdriving. Moreover, as shown in the foregoing examples, the naphthalenederivative of the present invention can be easily produced and iscolorless and chemically stable. Accordingly, the liquid crystalcomposition comprising the naphthalene derivative of the presentinvention is extremely useful as a practical liquid crystal composition,particularly a liquid crystal composition which can operate within awide temperature range and requires a high speed response and a lowvoltage driving.

1. A naphthalene derivative represented by the following general formula(I):

wherein R^(a) represents a C₁₋₂₀ alkyl, alkoxy, alkoxyalkyl, alkenyl oralkenyloxy group which may be substituted by a C₁₋₇ alkoxyl group orfrom 1 to 7 fluorine atoms; a and b each represent an integer, where ais 1 and b is 0 or 1; ring A represents an unsubstituted 1,4-phenylenegroup, 3-fluoro-1,4-phenylene group or 3,5-difluoro-1,4-phenylene group;ring B represents a trans-1,4-cyclohexylene group, 1,4-phenylene groupwhich maybe substituted by one or more fluorine atoms, pyridine-2,5-diylgroup, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group,pyridazine-3,6-diyl group, trans-1,3-dioxane-2,5-diyl group,trans-decahydronaphthalene-2,6-diyl group ortetrahydronaphthalene-2,6-diyl group; L^(a) represents —CH₂CH₂—,—CH₂CH₂CH₂CH₂—, —CH═CH—, —CH═CHCH₂CH₂—, —CH₂CH₂CH═CH—, —CH(CH₃)CH₂—,—CH₂CH(CH₃)—, —CF═CF—, —CF₂O—, —OCF₂—, —COO—, —OCO—, —C≡C— or singlebond, and L^(b) represents —CH₂CH₂CH₂CH₂—, —CH═CH—, —CH═CHCH₂CH₂—,—CH₂CH₂CH═CH—, —CH(CH₃)CH₂—, —CH₂CH(CH₃)—, —CF═CF—, —CF₂O—, —OCF₂—,—COO—, —OCO—, —C≡C— or single bond with the proviso that when ring Arepresents an unsubstituted 1,4-phenylene group, L^(b) represents asingle bond and b=1; and Z^(a) represents a fluorine atom, chlorineatom, trifluoromethoxy group, C₁₋₂₀ alkyl, alkoxyl, alkenyl oralkenyloxy group wherein the C₁₋₂₀ alkyl, alkoxyl, alkenyl or alkenyloxygroup may be substituted by a C₁₋₇ alkoxy group or from 1 to 7 fluorineatoms provided that when Z^(a) is a C₁₋₂₀ alkoxy group, Z^(a) is notsubstituted by an alkoxy group, or group represented by the followinggeneral formula (IIa) or (IIIb):

wherein L^(c) represents —CH₂CH₂—, —CH₂CH₂CH₂CH₂—, —CH═CH—,—CH═CHCH₂CH₂—, —CH₂CH₂CHCH—, —CH(CH₃)CH₂—, —CH₂CH(CH₃)—, —CF═CF—,—CF₂O—, —OCF₂—, —OCO—, —C≡C— or single bond; L^(d) represents —CH₂CH₂—,—CH₂CH₂CH₂CH₂—, —CH═CH—, —CH═CHCH₂CH₂—, —CH₂CH₂CH═CH—, —CH(CH₃)CH₂—,—CH₂CH(CH₃)—, —CF═CF—, —CF₂O—, —OCF₂—, —COO—, —OCO—, —C≡C— or singlebond; ring C represents a trans-1,4-cyclohexylene group, 1,4-phenylenegroup which may be substituted by one or more fluorine atoms,pyrazine-2,5-diyl group, pyridazine-3,6-diyl group,trans-1,3-dioxane-2,5-diyl group, trans-dechydronaphthalene-2,6-diylgroup or tetrahydronaphthalene-2,6-diyl group; ring D represents atrans-1,4-cyclohexylene group, 1,4-phenylene group which may besubstituted by one or more fluorine atoms, pyridine-2,5-diyl group,pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, pyridazine-3,6-diylgroup, trans-1,3-dioxane-2, 5-diyl group,trans-dechydronaphthalene-2,6-diyl group ortetrahydronaphthalene-2,6-diyl group; Z^(b) represents a fluorine atom,chlorine atom, bromine atom, iodine atom, hydrogen atom, cyano group,—SCN, OCN, —R′, —OR′, or —OCOR′ wherein R′ represents a C₁₋₂₀ alkyl oralkoxy group or C₂₋₂₀ alkenyl or alkenyloxy group and these groups maybe substituted by a C₁₋₁₀ alkoxyl, acyl, acyloxy or alkoxycarbonyl groupand one or more hydrogen atoms contained in these groups may besubstituted by one or more fluorine atoms, and in the case of forming anasymmetric carbon by the substitution or branching, it may form anoptically active form or racemic form, with the proviso that when Z^(a)represents formula (IIa) and ring C represents 1,4-phenylene group, thenthe phenylene group is substituted by a fluorine atom; and Z^(c)represents a fluorine atom, chlorine atom, bromine atom, iodine atom,hydrogen atom, cyano group, —SCN, OCN, —R′, —OR′, —OCOR′ or —COOR′,wherein R′ represents a C₁₋₂₀ alkyl or alkoxy group or C₂₋₂₀ alkenyl oralkenyloxy group and these groups may be substituted by a C₁₋₁₀ alkoxyl,acyl, acyloxy or alkoxycarbonyl group and one or more hydrogen atomscontained in these groups may be substituted by one or more fluorineatoms, and in the case of forming an asymmetric carbon by thesubstitution or branching, it may form an optically active form orracemic form.
 2. A naphthalene derivative represented by one of thefollowing general formulas:

wherein R represents a C₁₋₂₀ alkyl, but not a straight chain hexylgroup, alkoxy, alkoxyalkyl, alkenyl or alkenyloxy group which may besubstituted by a C1-7 alkoxyl group or from 1 to 7 fluorine atoms; and Zrepresents a fluorine atom, chlorine atom, trifluoromethoxy group, C₁₋₂₀alkyl, alkoxyl, alkenyl or alkenyloxy group wherein the C₁₋₂₀ alkyl,alkoxyl, alkenyl or alkenyloxy group may be substituted by a C₁₋₇ alkoxygroup or from 1 to 7 fluorine atoms provided that when Z is a C₁₋₂₀alkoxy group, Z is not substituted by an alkoxy group.
 3. A naphthalenederivative represented by the following general formula:

wherein R^(a) represents a C₁₋₂₀ alkyl, alkoxy, alkoxyalkyl, alkenyl oralkenyloxy group which may be substituted by a C₁₋₇ alkoxyl group orfrom 1 to 7 fluorine atoms; a and b each represent an integer, where ais 1 and b is 0 or 1; ring A represents an unsubstituted 1,4-phenylenegroup, 3-fluoro-1,4-phenylene group or 3,5-difluoro-1,4-phenylene group,and ring B represents a trans-1,4-cyclohexylene group, 1,4-phenylenegroup which may be substituted by one or more fluorine atoms,pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diylgroup, pyridazine-3,6-diyl group, trans-1,3-dioxane-2,5-diyl group,trans-decahydronaphthalene-2,6-diyl group ortetrahydronaphthalene-2,6-diyl group; L^(a) represents —CH₂CH₂—,—CH₂CH₂CH₂CH₂—, —CH═CH—, —CH═CHCH₂CH₂—, —CH₂CH₂CH═CH—, —CH(CH₃)CH₂—,—CH₂CH(CH₃)—, —CF═CF—, —CF₂O—, —OCF₂—, —COO—, −OCO—, —C≡C— or singlebond; and Z^(a) represents a fluorine atom, chlorine atom,trifluoromethoxy group, C₁₋₂₀ alkyl, alkoxyl, alkenyl or alkenyloxygroup wherein the C₁₋₂₀ alkyl, alkoxyl, alkenyl or alkenyloxy group maybe substituted by a C₁₋₇ alkoxy group or from 1 to 7 fluorine atomsprovided that when Z^(a) is a C₁₋₂₀ alkoxy group, Z^(a) is notsubstituted by an alkoxy group, or group represented by the followinggeneral formula (IIa) or (IIb):

wherein L^(c) represents —CH₂CH₂—, —CH₂CH₂CH₂CH₂—, —CH═CH—,—CHCHCH₂CH₂—, —CH₂CH₂CH═CH—, —CH(CH₃)CH₂—, —CH₂CH(CH₃)—, —CF═CF—,—CF₂O—, —OCF₂—, —OCO—, —C═C— or single bond; L^(d) represents —CH₂CH₂—,—CH₂CH₂CH₂CH₂—, —CH═CH—, —CH═CHCH₂CH₂—, —CH₂CH₂CH═CH—, —CH(CH₃)CH₂—,—CH₂CH(CH₃)—, —CF═CF—, —CF₂O—, —OCF₂—, —COO—, —OCO—, —C≡C— or singlebond; ring C represents a trans-1,4-cyclohexylene group, 1,4-phenylenegroup which may be substituted by one or more fluorine atoms,pyrazine-2,5-diyl group, pyridazine-3,6-diyl group,trans-1,3-dioxane-2,5-diyl group, trans-dechydronaphthalene-2,6-diylgroup or tetrahydronaphthalene-2,6-diyl group; ring D represents atrans-1,4-cyclohexylene group, 1,4-phenylene group which may besubstituted by one or more fluorine atoms, pyridine-2,5-diyl group,pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, pyridazine-3,6-diylgroup, trans-1,3-dioxane-2,5-diyl group,trans-dechydronaphthalene-2,6-diyl group ortetrahydronaphthalene-2,6-diyl group; Z^(b) represents a fluorine atom,chlorine atom, bromine atom, iodine atom, hydrogen atom, cyano group,—SCN, OCN, —R′, —OR′, or —OCOR′ wherein R′ represents a C₁₋₂₀ alkyl oralkoxy group or C₂₋₂₀ alkenyl or alkenyloxy group and these groups maybe substituted by a C₁₋₁₀ alkoxyl, acyl, acyloxy or alkoxycarbonyl groupand one or more hydrogen atoms contained in these groups maybesubstituted by one or more fluorine atoms, and in the case of forming anasymmetric carbon by the substitution or branching, it may form anoptically active form or racemic form, with the proviso that when Z^(a)represents formula (IIa) and ring C represents 1,4-phenylene group, thenthe phenylene group is substituted by a fluorine atom; and Z^(c)represents a fluorine atom, chlorine atom, bromine atom, iodine atom,hydrogen atom, cyano group, —SCN, OCN, —R′, —OR′, —OCOR′ or —COOR′,wherein R′ represents a C₁₋₂₀ alkyl or alkoxy group or C₂₋₂₀ alkenyl oralkenyloxy group and these groups may be substituted by a C₁₋₁₀ alkoxyl,acyl, acyloxy or alkoxycarbonyl group and one or more hydrogen atomscontained in these groups maybe substituted by one or more fluorineatoms, and in the case of forming an asymmetric carbon by thesubstitution or branching, it may form an optically active form; andwhen ring A represents an unsubstituted 1,4-phenylene group, b=1.
 4. Anaphthalene derivative according to claim 1, which has the structure:


5. A naphthalene derivative according to claim 1, which has thestructure: